Pyridine sulfonyl urea derivatives

ABSTRACT

The present invention relates to novel pyridinesulfonylurea derivatives, having a herbicidal activity, which is described in the following structure of general formula (I) ##STR1## wherein, Q is Q-1, Q-2, Q-3 or Q-4 as follows; ##STR2## E is single bond or CH 2  R 2  is C 1  -C 6  alkyl substituted with 1 to 3 halogens; 
     R 1 , R 3 , W and A are defined in the claims; and these may be an agriculturally suitable salt.

This application is a 371 of PCT/KR92/0005, filed Feb. 25, 1992.

TECHNICAL FIELD

The present invention relates to novel pyridine sulfonyl ureaderivatives having agriculturally suitable for herbicidal activity.

BACKGROUND OF THE INVENTION

It is publicly well known that sulfonyl urea derivatives have aherbicidal activity. Here are the formulas for the sulfonyl ureas.

1) U.S. Pat. No. 4,332,611 discloses the compound having the followingformula ##STR3## wherein, L is OH, ##STR4## R is H, F, Cl, Br, NO₂, CF₃or C₁ -C₃ alkyl or alkoxy; R¹ is H or C₁ -C₄ alkyl;

R² is H or CH₃ ;

R⁸ is H, CH₃ or OCH₃ ;

A is pyrimidine or triazine.

2) U.S. Pat. No. 4,786,314 discloses the compound having the followingformula ##STR5## wherein, R¹ is F, Cl, Br, C₁ -C₄ alkyl, OH, alkoxy,alkylthio or C₁ -C₂ alkyl substituted with phenyl group;

R² is --CHR--CN etc.

3) U.S. Pat. No. 4,838,926 discloses the compound having the followingformula ##STR6## wherein, Q is C₁ -C₄ alkyl substituted with R² ;

R² is OR³, ##STR7## R³ is H, C₁ -C₄ alkyl; L is ##STR8## R¹² is H orCH₃. 4) European Patent No. 125,205 discloses the compound having thefollowing formula ##STR9## wherein, R⁶ is H, alkyl or F;

R⁷ is H or CH₃ ;

W is O or S;

R⁸ is haloalkyl or alkoxyalkyl.

5) U.S. Pat. No. 4,348,220 discloses the compound having the followingformula ##STR10## wherein, L is OR⁹ ;

R¹ is H or C₁ -C₄ alkyl;

R² is H or CH₃ ;

R⁹ is C₁ -C₆ alkyl.

6) U.S. Pat. No. 4,822,403 discloses the compound having the followingformula ##STR11## wherein, n is 0 or 1;

W is C₂ -C₈ alkenyl substituted with 1˜3 F, Cl, Br, OH or alkoxy.

7) U.S. Pat. No. 4,662,933 discloses the compound having the followingformula ##STR12## wherein, Q is linear --(CH₂)_(n) -substituted with C₁-C₃ haloalkyl;

n is an integer of 1˜3;

R² is SH, N₃ or SCN.

8) European Patent No. 13,480 discloses the compound having thefollowing formula ##STR13## wherein, R¹ is H, Cl, Br, F, alkyl, alkoxy,alkylthio or CO₂ R⁵.

9) U.S. Pat. Nos. 4,435,206 and 4,522,645 disclose 2-pyridine sulfonylurea substituted with R¹ on 3-position, wherein R1 is H, Cl, Br, F,alkyl, alkoxy, alkylthio, CO₂ R⁵ or SO₂ NR⁶ R⁷.

10) U.S. Pat. No. 4,339,267 discloses 3-pyridine sulfonyl urea compoundhaving the following formula ##STR14## wherein, R⁴ is H, Cl, Br, F,alkyl, alkoxy, NO₂, CO₂ R⁶ or SR¹³.

11) European Patent No. 30,433 disclose the compound having thefollowing formula ##STR15## wherein, R³ is H, Cl, Br, F, CO₂ R¹¹ orSOnR¹².

12) U.S. Pat. No. 4,456,469 discloses the compound having the followingformula ##STR16## wherein, R is alkyl, alkenyl, CF₃, CHF₂ or CH₂ CF₃ ;

Z is H, F, Cl, Br or SCH₃.

13) U.S. Pat. No. 4,487,626 discloses 2,3- or 4-substituted pyridinesulfonyl urea compound having the following formula ##STR17## wherein, Ais ##STR18## R² is H, Cl, Br, F, alkyl, alkoxy, CO₂ R⁵, SOmR⁶, SO₂ NR¹⁸R¹⁹ or SO₂ N(OCH₃)CH₃.

14) U.S. Pat. Nos. 4,421,550 and 4,496,392, and European Patents No.125,846/155,767/161,905/164,269/171,286 disclose pyridine sulfonyl ureasubstituted with Cl, Br, SO₂ R or SO₂ NR¹ R² on 2- or 3-position.

15) U.S. Pat. No. 4,549,898 discloses pyridine sulfonyl urea compoundhaving the following formula ##STR19## wherein, R² is H, alkyl,haloalkyl, halogen, NO₂, alkoxy, ##STR20## SO₂ NR⁶ R⁷ or SOnR; R³ is H,halogen, alkyl, OCH₃, NO₂ or CF₃ ;

R⁵ is H, NO₂, F, Cl, Br, CH₃, CF₃, SOn alkyl, --CO₂ R or alkoxy.

16) U.S. Pat. No. 4,579,583 discloses pyridine sulfonyl urea compoundhaving the following formula ##STR21## wherein, X is O, S, SO or SO₂ ;

A is a optionally substituted alkyl, alkenyl or alkynyl;

R¹ is H, halogen, alkyl, alkoxy, haloalkyl, alkylthio or alkylsulfonyl.

17) U.S. Pat. No. 4,518,776 discloses a method for preparing thecompound having the following formula ##STR22## wherein, R¹ isalkylsulfonyl or dialkylamino sulfonyl group;

R² is H, halogen, No₂, CF₃, alkyl or alkoxy.

18) European Patent No. 101,670 discloses manufacture of pyridinesulfonyl urea having the following formula ##STR23## wherein, R¹ is Qalkyl or SO₂ N R⁴ R⁵ ;

Q is S or SOn;

R² is H, halogen, CF₃, NO₂, alkyl or alkoxy.

19) U.S. Pat. No. 4,521,597 discloses manufacture of pyridine sulfonylurea compound having the following formula ##STR24## wherein, R³ is H,F, Cl, Br, NO₂, OCH₃ or CF₃ ;

R⁵ is SOm alkyl or SO₂ NR⁸ R⁹ ;

R⁶ is H, F, CH₃ or OCH₃.

20) European Patent No. 184,385 discloses the compound having thefollowing formula ##STR25## 21) U.S. Pat. No. 4,747,870 disclosesO-alkylcarbonyl pyridine sulfonyl urea compound, and U.S. Pat. No.4,838,926 discloses O-substituted alkylpyridine urea compound. And, U.S.Pat. No. 4,747,337 discloses the compound having the following formula##STR26## wherein, J is ##STR27## R¹ is H, alkyl, haloalkyl, halogen,NO₂, alkoxy, alkylthio or CN;

R² -R⁶ are alkylthio, alkylsulfinyl, alkylsulfonyl, cycloalkylthio, SO₂R⁸, SO₃ R⁸ N₃, CN, CH₂ F, CHF₂, CH₂ Cl, haloalkyl or PO(O alkyl)₂.

As the above patents, many sulfonyl urea herbicides have known untilrecently.

Even with these herbicides, more and more weeds develop immunityforwards these herbicides and cause undesirable vegetations. Thus,continuous research is in demand to develop more effective and newer fora good harvest.

Therefore, the object of the presentation is to invent a new pyridinesulfonyl urea derivative having a very prominent herbicidal activitywith a good selectivity for various vegetations and agriculturallysuitable herbicides for treatment of pre-emergence and/or post-emergenceor plant growth regulants.

SUMMARY OF THE INVENTION

The present invention relates to novel pyridine sulfonyl ureaderivatives having the following formula (I) ##STR28## wherein, P isP-1, P-2, P-3 or P-4 as follows; ##STR29## E is single bond or CH₂ ; R¹is H, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, halogen, CN, NO₂, C₁ -C₃ alkoxy,C₁ -C₃ haloalkoxy, SO₂ NR^(I) R^(II), C₁ -C₃ alkylthio, C₁ -C₃alkylsulfinyl, C₁ -C₃ alkylsulfonyl, SCH₂ F, NH₂, NHCH₃, N(CH₃)₂, C₁ -C₂alkyl substituted with C₁ -C₂ alkoxy, C₁ -C₂ haloalkoxy, SH, SCH₃, CN orOH or CO₂ R^(III) ; and then R^(I) is H, C₁ -C₄ alkyl, C₂ -C₃cyanoalkyl, methoxy or ethoxy; R^(II) is H, C₁ -C₄ alkyl, C₃ -C₄alkenyl, or when taken together, connecting R^(I) and R^(II), --(CH₂)₃--, --(CH₂)₄ --, --(CH₂)₅ -- or CH₂ CH₂ OCH₂ CH₂ --, may be formed;

R^(III) is C₁ -C₄ alkyl, C₃ --C₄ alkenyl, C₃ -C₄ alkynyl, C₁ -C₄ alkylsubstituted with 1˜2 halogen or cyano groups, C₅ -C₆ cycloalkyl, C₃ -C₇cycloalkylalkyl or C₂ -C₄ alkoxyalkyl;

R² is C₁ -C₆ alkyl substituted with 1˜3 halogen;

R³ is H or CH₃ ;

W is O or S;

A is A1, A2, A3, A4, A5, A6 or A7 as following; ##STR30## wherein, X isH, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkyl, C₁-C₄ haloalkylthio, C₁ -C₄ alkylthio, halogene, C₂ -C₅ alkoxyalkyl, C₂-C₅ alkoxyalkoxy, amino, C₁ -C₃ alkylamino, di(C₁ -C₃ alkyl) amino or C₃-C₅ cycloalkyl;

Y is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄haloakylthio, C₁ -C₄ alkylthio, C₂ -C₅ alkoxyalkyl, C₂ -C₅ alkoxyalkoxy,amino, C₁ -C₃ alkylamino, di(C₁ -C₃ alkyl)amino, C₃ -C₄ alkenyloxy, C₂-C₅ alkylthioalkyl, C₁ -C₄ haloalkyl, C₂ -C₄ alkynyl, azido, cyano, C₂-C₅ alkylsulfinylalkyl, C₂ -C₅ alkylsulfonylalkyl, CH₂ OH, C₃ -C₅cycloalkyl, C₃ -C₅ cycloalkoxy, C₃ -C₄ alkynyloxy, ##STR31## m is 2 or3; L¹ and L² are independently O or S;

R⁴ and R⁵ are independently C₁ -C₂ alkyl;

R⁶ is H, or CH₃ ;

Z is CH, N, CCH₃ or CC₂ H₅ ;

Y¹ is O or CH₂ ;

X¹ is CH₃, OCH₃, OC₂ H₅ or OCHF₂ ;

Y³ is H or CH₃ ;

Y² is CH₃, CH₂ CH₃, OCH₃, OCH₂ CH₃, SCH₃ or SCH₂ CH₃ ;

X² is CH₃, CH₂ CH₃, or CH₂ CF₃ ;

X³ is CH₃ or OCH₃ ;

Y⁴ is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃ or Cl;

X⁴ is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃ or Cl; and these may be anagriculturally suitable salt, and then,

(1) if X is Cl, Br, F or I, Z is CH and Y is OCH₃, OC₂ H₅, NCH₃ (OCH₃),NH₂, NHCH₃, N(CH₃)₂ or OCHF₂ ;

(2) if X or Y is OCHF₂, Z is CH;

(3) X⁴ and Y⁴ are not Cl simultaneously;

(4) if W is S, R³ is H, A is A₁, Z is CH or N and, Y is CH₃, OCH₃, OCH₂CH₃, CH₂ OCH₃, C₂ H₅, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂ CH₂OCH₃, CH(OCH₃)₂ or ##STR32## (5) if a number of total carbon atoms X andY are more than 4, a number of carbon atoms of R² is 4 or less than 4.

DETAILED DESCRIPTION OF THE INVENTION

Among the definitions according to the present invention, the followingterms have the following meanings;

a) "Alkyl" used ether alone or in compound word such as "alkylthio" or"haloalkyl" etc. denotes straight chain or branched alkyls such asmethyl, ethyl, n-propyl, isopropyl or buthyl isomers.

b) "Alkoxy" denotes methoxy, ethoxy, n-propoxy, isopropoxy or buthoxyisomers.

c) "Alkenyl" denotes straight chain or branched alkenes, for example,vinyl, 1-prophenyl, 2-prophenyl, or buthenyl, pentenyl, hexenyl orheptenyl isomers etc.

d) "Alkynyl" denotes straight chain or branched alkynyl such as ethynyl,1-propynyl, 2-propynyl, or buthynyl, pentynyl or hexynyl isomers.

e) "Halogen" used ether alone or in compound ward "halo" denoteschlorine, fluorine, bromine or Iodine.

A preferred group of pyridine sulfonyl urea derivatives having theformula shown as the below (I), in view of compounding of the polymerand herbicidal activity, wherein

(1) R³ is H, W or O;

(2) R¹ is H, F, Cl, C₁ -C₂ alkyl, C₁ -C₂ haloalkyl, C₁ -C₂ alkoxy, C₁-C₂ haloalkoxy, C₁ -C₂ alkylthio, CH₂ OCH₃, or CH₂ SCH₃ ;

(3) X is CH₃, OCH₃, OCH₂ CH₃, Cl, F, Br, OCHF₂, CH₂ F, OCH₂ CH₂ F, OCH₂CHF₂, OCH₂ CF₃, CF₃, CH₂ Cl or CH₂ Br;

Y is H, C₁ -C₃ alkyl, OCH₃, OCH₂ CH₃, CH₂ OCH₃, NHCH₃, NCH₃ (OCH₃),N(CH₃)₂, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OC₂ H₅, OCH₂ CH₂OCH₃, CH₂ SCH₃, OCHF₂, SCHF₂, cyclopropyl, C.tbd.CH, or C.tbd.C--CH₃ ;

(4) R² is CH₂ F, CHF₂, CHFCl, CH₂ Cl, CH₂ Br, CHFCH₃, CH₂ CH₂ F, CH₂ CH₂Cl, CHClCH₃, CHCl₂, CHFCH₂ F, CHClCH₂ Cl, CHFCH₂ Cl or CH₂ CF₃ ;

(5) A is A₁, and Z is CH;

X is CH₂ OCH₃, OCH₂ CH₃, Cl or OCHF₂ ;

Y is CH₃, C₂ H₅, OCH₃, CH₂ OCH₃, CH(OCH₃)₂, OCHF₂, NHCH₃, N(Me)₂ orcyclopropyl, and R¹ is H, CH₃, OCH₃ or Cl.

The novel compounds having the above formula(I) according to the presentinvention have a very strong herbicidal activity and a good selectivityfor a useful vegetation.

The compounds of the present invention can be prepared by reactions asdescribed in herein below.

The compound of general formula(I) can be obtained by hydrolyzing thecompound of following formula(II) with alkali under water, organicsolvent or the mixture solution thereof.

(Method 1) ##STR33## wherein, ##STR34## and R¹ is not para substituentof sulfonyl urea.

In the above reaction scheme of Method 1, Ac is acetyl group, but it maybe a protecting group easily dissolved by acid, alkali or others. Inorder to hydrolyze the above Ac group, alkali base such as NaOH, KOH,LiOH, Na₂ CO₃, K₂ CO₃, etc., preferably LiOH, may be used.

The above reaction of Method I is carried out under water or organicsolvent, and also a mixture of water with unreacting solvent such asmethanol, ethanol, acetone or THF etc., or solvent alone.

The hydrolysis in the reaction occurs at the temperature of 0°˜80° C.and the reaction time of 1˜24 hours, and then the obtained product maybe easily seperated by acidifying with HCl water solution.

As an other process, after acidifying, the obtained product is extractedwith methylene chloride, ethyl acetate, etc. thenconcentrated/crystallized to obtain the final product. If necessary, apure product can be obtained by purification to column chromatograph.

The compound of the above formula(I) according to the present inventioncan be prepared by reaction the compound having the followingformula(III) with alkali at the temperature of 25°˜40° C. (Method 2)##STR35##

The reaction of Method 2 may be preferably carried out under alkali suchas NaOH etc. of a small quantity. The product may be seperated as thesame with the above Method I.

On the other hand, the compound of the above formula(II) used in thepresent invention can be prepared by reacting the compound of followingformula(IV) with formula(V). ##STR36##

The above reaction may be carried out in solvent of dioxane oracetonitryl under in active atmosphere at the temperature of 25° C. for1˜2 hours. The obtained product may be easily seperated by acidifyingwith HCl water solution.

As another process, after acidifying, the obtained product is extractedwith solvent of methylene chloride or ethylacetate and dried/evaporatedto obtain final product.

Also, the compound of the above formula(III) used in the presentinvention can be obtained by the method disclosed on U.S. Pat. No.4,370,480.

Meanwhile, phenylcarbamate(V) used for preparing the above formula(II)can be composed by reacting heterocyclic amine of A-NHR³ of formula(VI)with diphenylcarbonate or phenylchloroformate under a base such as NaH,pyridine, K₂ CO₃, etc. after adding of dimethyl aminopyridine(DMAP), andthen the reacting mixture is stirred in a solvent such as THF etc. at25°˜65° C. for 12˜36 hours. ##STR37##

The compound of the formula(IV) can be prepared by treatingN-t-buthylsulfonamide(IV) with an acid such as trifluoroaceticacid(TFA), polyphosphoric acid(PPA) or p-toluensulfonic acid(p-TSA).##STR38##

In order to prepare the above formula(IV), the compound of the aboveformula(VII) is added in trifluoroacetic acid (about 0.3M) of an excess.And they are stirred at about 25° C. for 1˜72 hours to easily carry outthe reaction.

Then, a volatile metter is evaporated under vacuum and the residue iscrystallized in a solvent such as diethylether, 1-chlorobutane,ethylacetate, etc. to isolate the product, sulfonamide of formula(IV).This reaction shall be referenced by J. D. Catt and W. L. Matier, J.Org. Chem., 38, 1974(1973).

Also, sulfonamide of the above formula(IV) can be prepared by thefollowing reaction process. ##STR39##

As the above reaction, the compound of formula(IV) can be obtained byadding ammonia of a great quantity in sulfonylchloride, preferablytemperature below -10° C., and as a solvent such as ethylacetate, ether,THF, methylene chloride etc. may be used.

On the other hand, the compound of the above formula(VII) can beprepared by the following reaction process. ##STR40## (wherein, L is H,OC₂ H₅, NMe₂ or N(OCH₃)CH₃)

In the above reaction, n-butyl lithium of 2 equivalents is added in thecompound of the above formula(IXa) in order to lithiation; andthereafter aldehide, ester or amide taking ketone compound, orN,O-dimethyl hydroxyamide is added; if aldehide is used, hydroxycompound is produced directly; and then the compound of formula(VIIa)can be prepared by acylation under pyridine; if the compound of R² CHOis not obtained, after obtaining ketone compound then hydroxy compoundbe obtained by reduction of that with NaBH₄ ; and then the compound offormula(VIIa) is easily obtained by acylation.

This reaction process is able to be carried out by a skill person inthis technical field.

Also, in the case of 2-pyridine sulfonamide, the compound offormula(VIIa) can be obtained by the same with the above reactionprocess. ##STR41##

Also, sulfonamide can be obtained by reacting sulfonylchloride(VIII)with t-BuNH₂ as the following reaction scheme. ##STR42##

In the above reaction, sulfonylchloride can be prepared by the method ofU.S. Pat. Nos. 4,456,469 or 4,740,233 as following scheme. ##STR43##

Wherein, the reaction may be preferably carried out at low temperatureof 10° C. and below it.

The compound of formula(XII) can be prepared by the following reactionscheme. ##STR44##

This reaction is disclosed in U.S. Pat. No. 4,420,325.

The compound of formula(XI) can be prepared by the following reactionprocess. ##STR45##

In the reaction process, metalation reaction using LDA of2-fluoropyridine may be carried out by the method of T, Gungor, F.Marsais and G. Gueguiner, J. Organomet Chem., 1981, 215, 139-150, andthereafter acylation by a common method.

Halopyridin of the above formula(XV) is transformed to sulfide offormula(XIV) by reating with a mercaptane under a base. This reaction isdisclosed by U.S. Pat. No. 4,456,469.

Lithiation of fluoropyridine or transform reaction to sulfonyl chloridewhich is consisted of transformation to sulfide from fluoropyridin andits chloridization, can be easily carried out by the method of U.S. Pat.No. 4,774,337.

The compound of formula(XVI) can be composed by the following reactionprocess. ##STR46##

It was well-known the reaction which is transformed aminopyridine tosulfonamide as preferably reference of U.S. Pat. No. 4,456,459. Also,exchange reaction to metal halogen from bromosulfonamide was well-known,and thereafter sulfonamide(XVI) may be prepared by the above reactionscheme for manufacturing the above formula(VIIa).

The heterocyclic amine compound of formula(VI) may be prepared by askill person in this technical field from a method disclosed inliteratures or the simple transformation of it.

For example, European Patent Application No. 84,244 (Pub. Jul. 27, 1983)and J. Am. Chem. Soc., 69,3072(1947) of W. Braker et al. disclose amethod for preparing aminopyrimidine and triazine substituted withacetyl group. European Patent No. 72,347 and U.S. Pat. Nos.4,443,243/4,487,915 disclose a method for preparing aminopyrimidineand/or triazine substituted with haloalkyl such as OCHF₂, SCHF₂, OCH₂CH₂ F and OCH₂ CF₃ etc. and haloalkylthio as a substitution group.

European Patent No. 108,708, U.S. Pat. Nos. 4,515,626/4,600,428 disclosecyclo propylpyrimidine and/or triazine substituted with alkyl,haloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamio and alkoxyalkylgroup etc.

European Patent No. 15,863 discloses a method for preparing the compoundof the above formula(VI), as 5,6-dihydro-puro[2,3-d]pyrmidine-2-aminecompounds and cyclopenta[d]pyrimidine-2-amine compounds which A is A₂ ;and 6,7-dihydro-5H-pyrano-[2,3-d]pyrimidine-2-amine compound which A isA₃.

European Patent No. 46,677 discloses puro[2,3-d]pyridine-2-aminecompounds which A is A₄ in the formula(VI), and European Patent No.73,562 discloses heterocyclic compounds which A is A₅.

The compound of formula(VI) which A is A₆ can be prepared by EuropeanPatent No. 94,260. The compound of formula(VI) which A is A₇, can bemanufactured by the method of European Patent No. 125,864.

Common methods for preparing aminopyridine and triazine compounds isarranged on the following literatures:

"The chemistry and Heterocyclic compounds", Series, IntersciencePublishers, Inc., New York and London; "Pyrimidines", Vol. 16, D. J.Brown Ed.; "S-Triazines and Derivatives", Vol. 13, E. M. Smolin and L.Rapaport. Composition of triazine compounds is disclosed in F. C.Schaefer, U.S. Pat. No. 3,154,547 and K. R. Huffman and F. C. Schaefer,J. Org. Chem., 28, 1812(1963).

On the other hand, salts of the compound of the above formula(I) also isuseful as herbicide, and they can be prepared by various methodsaccording to prior art.

For example, metal salts of the compound can be prepared by reacting theabove formula(I) compound with strong basic anion, e.g. alkali oralkaline earth metal solution having hydroxyl group alkoxyde orcarbonate, and also quaternary amine salt alike.

A salt of the formula(I) compound may also be obtained by cationexchange. The cation exchange can be manufactured by directly reactingsolution containing cation for exchange with solution of salt offormula(I), for example aqueous solution of alkali metal or quaternaryamine salt.

This method is useful when the desirable salt is water soluble,especially sodium, potassium or calcium salt.

The above manufacturing methods is summarized briefly, but the methodcan be carried out easily by a skill person in this technical field ofcomposition and manufacturing for sulfonyl urea or organic composition.

The compounds of said general formula(I) of the present inventionspecify the following Table;

                                      TABLE 1                                     __________________________________________________________________________     ##STR47##                                                                    R.sup.1                                                                             R.sup.2                                                                              R.sup.3                                                                           X       Y         mp (°C.)                            __________________________________________________________________________    H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.3 119-120                                    H     CH.sub.2 F                                                                           H   CH.sub.3                                                                              OCH3      151-152                                    H     CH.sub.2 F                                                                           H   CH.sub.3                                                                              CH.sub.3  169-170                                    H     CH.sub.2 F                                                                           H   Cl      OCH.sub.3 138-139                                    H     CH.sub.2 F                                                                           H   Br      OCH.sub.3                                            H     CH.sub.2 F                                                                           H   H       CH.sub.3                                             H     CH.sub.2 F                                                                           H   OHC.sub.3                                                                             H                                                    H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             CH.sub.2 OC.sub.2 H.sub.5                            H     CH.sub.2 F                                                                           H   OCF.sub.2 H                                                                           OCH.sub.3                                            H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             CH(OCH.sub.3).sub.2                                  H     CH.sub.2 F                                                                           H   CH.sub.3                                                                              OC.sub.2 H.sub.5                                     H     CH.sub.2 F                                                                           H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                   H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             CH.sub.2 OCH.sub.3                                   H     CH.sub.2 F                                                                           H   C.sub.2 H.sub.5                                                                       OCH.sub.3                                            H     CH.sub.2 F                                                                           H   OC.sub.2 H.sub.5                                                                      OCH.sub.3                                            H     CH.sub.2 F                                                                           H   OCH.sub.2 CF.sub.3                                                                    OCH.sub.3                                            H     CH.sub.2 F                                                                           H   CF.sub.3                                                                              OCH.sub.3                                            H     CH.sub.2 F                                                                           H   CH.sub.2 F                                                                            OCH.sub.3                                            H     CH.sub.2 F                                                                           H   CH.sub.2 Cl                                                                           OCH.sub.3                                            H     CH.sub.2 F                                                                           H   CH.sub.2 Br                                                                           OCH.sub.3                                            H     CH.sub.2 F                                                                           H   F       OCH.sub.3                                            H     CH.sub.2 F                                                                           H   I       OCH.sub.3                                            H     CH.sub.2 F                                                                           H   OCH.sub.2 CH.sub.2 F                                                                  OCH.sub.3                                            H     CH.sub.2 F                                                                           H   OCH.sub.2 CH.sub.2 CF.sub.3                                                           OCH.sub.3                                            H     CH.sub.2 F                                                                           H   OCH.sub.2 CHF.sub.2                                                                   CH.sub.3                                             H     CH.sub.2 F                                                                           H   OCH.sub.2 CF.sub.3                                                                    CH.sub.3                                             H     CH.sub.2 F                                                                           H   Cl      OC.sub.2 H.sub.5                                                                        133-135                                    H     CH.sub.2 F                                                                           H   OC.sub.2 H.sub.5                                                                      NHCH.sub.3                                           H     CH.sub.2 F                                                                           H   OC.sub.2 H.sub.5                                                                      CH.sub. 2 SCH.sub.3                                  H     CH.sub.2 F                                                                           H   OCF.sub.2 H                                                                           CH.sub.3                                             H     CH.sub.2 F                                                                           H   Cl      OCF.sub.2 H                                          H     CHFCH.sub.3                                                                          H   OCH.sub.3                                                                             OCH.sub.3 132-134                                    H     CHFCH.sub.3                                                                          H   CH.sub.3                                                                              OCH.sub.3 135-137                                    H     CHFCH.sub.3                                                                          H   CH.sub.3                                                                              CH.sub.3  146-148                                    H     CHFCH.sub.3                                                                          H   Cl      OCH.sub.3 119-121                                    H     CHFCH.sub.3                                                                          H   Br      OCH.sub.3                                            H     CHFCH.sub.3                                                                          H   CH.sub.3                                                                              H                                                    H     CHFCH.sub.3                                                                          H   OCH.sub.3                                                                             H                                                    H     CHFCH.sub.3                                                                          H   OCH.sub.3                                                                             CH.sub.2 OC.sub.2 H.sub.5                            H     CHFCH.sub.3                                                                          H   OCF.sub.2 H                                                                           OCH.sub.3                                            H     CHFCH.sub.3                                                                          H   OCH.sub.3                                                                             CH(OCH.sub.3).sub.2                                  H     CHFCH.sub.3                                                                          H   CH.sub.3                                                                              OC.sub.2 H.sub.5                                     H     CHFCH.sub.3                                                                          H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                   H     CHFCH.sub.3                                                                          H   OCH.sub.3                                                                             CH.sub.2 OCH.sub.3                                   H     CHFCH.sub.3                                                                          H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                      H     CHFCH.sub.3                                                                          H   OC.sub.2 H.sub.5                                                                      OCH.sub.3                                            H     CHFCH.sub.3                                                                          H   OCH.sub.2 CF.sub.3                                                                    OCH.sub.3                                            H     CHFCH.sub.3                                                                          H   CF.sub.3                                                                              OCH.sub.3                                            H     CHFCH.sub.3                                                                          H   CH.sub.2 F                                                                            OCH.sub.3                                            H     CHFCH.sub.3                                                                          H   CH.sub.2 Cl                                                                           OCH.sub.3                                            H     CHFCH.sub.3                                                                          H   CH.sub.2 Br                                                                           OCH.sub.3                                            H     CHFCH.sub.3                                                                          H   F       OCH.sub.3                                            H     CHFCH.sub.3                                                                          H   I       OCH.sub.3                                            H     CHFCH.sub.3                                                                          H   OCH.sub.2 CH.sub.2 F                                                                  OCH.sub.3                                            H     CHFCH.sub.3                                                                          H   OCH.sub.2 CH.sub.2 CF.sub.3                                                           OCH.sub.3                                            H     CHFCH.sub.3                                                                          H   OCH.sub.2 CHF.sub.2                                                                   CH.sub.3                                             H     CHFCH.sub.3                                                                          H   OCH.sub.2 CF.sub.3                                                                    CH.sub.3                                             H     CHFCH.sub.3                                                                          H   Cl      OC.sub.2 H.sub.5                                                                        112-113                                    H     CHFCH.sub.3                                                                          H   OC.sub.2 H.sub.5                                                                      NHCH.sub.3                                           H     CHFCH.sub.2 CH.sub.3                                                                 H   OCH.sub.3                                                                             CH.sub.3  124-125                                    H     CHFCH.sub.2 CH.sub.3                                                                 H   OCH.sub.3                                                                             OCH.sub.3 120-121                                    H     CHFCH.sub.2 CH.sub.3                                                                 H   Cl      OCH.sub.3 114-115                                    H     CH.sub.2 F                                                                           H   NH.sub.2                                                                              OC.sub.2 H.sub.5                                     H     CH.sub.2 F                                                                           H   n-C.sub.3 H.sub.7                                                                     OCH.sub.3                                            H     CH.sub.2 F                                                                           H   NHCH.sub.3                                                                            OCH.sub.3                                            H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             SCH.sub.3                                            H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             SCF.sub.2 H                                          H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.2 CCH                                        H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.2 CHCH.sub.2                                 H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             CCH                                                  H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             N(CH.sub.3).sub.2                                    H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             cyclopropyl                                          H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             NH.sub.2                                             H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             CF.sub.3                                             H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.2 CH.sub.2 OCH.sub.3                         H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             CH.sub.2 SCH.sub.3                                   H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             CHO                                                  H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             COCH.sub.3                                           H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             CH(SCH.sub.3)OC.sub.2 H.sub.5                        H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             C(CH.sub.3)(SCH.sub.3).sub.2                         H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             C(SC.sub.2 H.sub.5).sub.2                            H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             1,3-dioxolan-2-yl                                    H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             2-methyl-1,3-                                                                 oxathiolan-2yl                                       H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             1,3-oxathian-2-yl                                    H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             2-methyl-1,3-                                                                 dithian-2-yl                                         H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             4-methyl-1,3-                                                                 dioxolan-2-yl                                        H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             2-4-dimethyl-1,3-                                                             dithiolan-2-yl                                       H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             N(OCH.sub.3)(CH.sub.3)                               H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             CCCH.sub.3                                           H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                      H     CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCF.sub.2 Br                                         H     CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.3                                                                             OCH.sub.3                                            H     CH.sub.2 CH.sub.2 F                                                                  H   CH.sub.3                                                                              OCH.sub.3                                            H     CH.sub.2 CH.sub.2 F                                                                  H   CH.sub.3                                                                              CH                                                   H     CH.sub.2 CH.sub.2 F                                                                  H   Cl      OCH.sub.3                                            H     CH.sub.2 CH.sub.2 F                                                                  H   Br      OCH.sub.3                                            H     CH.sub.2 CH.sub.2 F                                                                  H   CH.sub.3                                                                              H                                                    H     CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.3                                                                             H                                                    H     CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.3                                                                             CH.sub.2 OC.sub.2 H.sub.5                            H     CH.sub.2 CH.sub.2 F                                                                  H   OCF.sub.2 H                                                                           OCH.sub.3                                            H     CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.3                                                                             CH(OCH.sub.3).sub.2                                  H     CH.sub.2 CH.sub.2 F                                                                  H   CH.sub.3                                                                              OC.sub.2 H.sub.5                                     H     CH.sub.2 CH.sub.2 F                                                                  H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                   H     CH.sub.2 CH.sub. 2 F                                                                 H   OCH.sub.3                                                                             CH.sub.2 OCH.sub.3                                   H     CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                      H     CH.sub.2 CH.sub.2 F                                                                  H   OC.sub.2 H.sub.5                                                                      OCH.sub.3                                            H     CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.2 CF.sub.3                                                                    OCH.sub.3                                            H     CH.sub.2 CH.sub.2 F                                                                  H   CF.sub.3                                                                              OCH.sub.3                                            H     CH.sub.2 CH.sub.2 F                                                                  H   CH.sub.2 F                                                                            OCH.sub.3                                            H     CH.sub.2 CH.sub.2 F                                                                  H   CH.sub.2 Cl                                                                           OCH.sub.3                                            H     CH.sub.2 CH.sub.2 F                                                                  H   CH.sub.2 Br                                                                           OCH.sub.3                                            H     CH.sub.2 CH.sub.2 F                                                                  H   F       OCH.sub.3                                            H     CH.sub.2 CH.sub.2 F                                                                  H   I       OCH.sub.3                                            H     CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.2 CH.sub.2 F                                                                  OCH.sub.3                                            H     CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.2 CH.sub.2 CF.sub.3                                                           OCH.sub.3                                            H     CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.2 CHF.sub.2                                                                   CH.sub.3                                             H     CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.2 CF.sub.3                                                                    CH.sub.3                                             H     CH.sub.2 CH.sub.2 F                                                                  H   Cl      OC.sub.2 H.sub.5                                     H     CH.sub.2 CH.sub.2 F                                                                  H   OC.sub.2 H.sub.5                                                                      NHCH.sub.3                                           H     CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.3                                                                             CH.sub.2 SCH.sub.3                                   H     CH.sub.2 CH.sub.2 F                                                                  H   OCF.sub.2 H                                                                           CH.sub.3                                             H     CH.sub.2 CH.sub.2 F                                                                  H   Cl      OCF.sub.2 H                                          H     CH.sub.2 Cl                                                                          H   OCH.sub.3                                                                             OCH.sub.3 135-137                                    H     CH.sub.2 Cl                                                                          H   CH.sub.3                                                                              OCH.sub.3 123-124                                    H     CH.sub.2 Cl                                                                          H   CH.sub.3                                                                              CH.sub.3  139-140                                    H     CH.sub.2 Cl                                                                          H   Cl      OCH.sub.3 136-137                                    H     CH.sub.2 Cl                                                                          H   Br      OCH.sub.3                                            H     CH.sub.2 Cl                                                                          H   CH.sub.3                                                                              H                                                    H     CH.sub.2 Cl                                                                          H   OCH.sub.3                                                                             H                                                    H     CH.sub.2 Cl                                                                          H   OCH.sub.3                                                                             CH.sub.2 OC.sub.2 H.sub.5                            H     CH.sub.2 Cl                                                                          H   OCF.sub.2 H                                                                           OCH.sub.3                                            H     CH.sub.2 Cl                                                                          H   OCH.sub.3                                                                             CH(OCH.sub.3).sub.2                                  H     CH.sub.2 Cl                                                                          H   CH.sub.3                                                                              OC.sub.2 H.sub.5                                     H     CH.sub.2 Cl                                                                          H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                   H     CH.sub.2 Cl                                                                          H   OCH.sub.3                                                                             CH.sub.2 OCH.sub.3                                   H     CH.sub.2 Cl                                                                          H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                      H     CH.sub.2 Cl                                                                          H   OC.sub.2 CF.sub.5                                                                     OCH.sub.3                                            H     CH.sub.2 Cl                                                                          H   OCH.sub.2 CF.sub.3                                                                    OCH.sub.3                                            H     CH.sub. 2 Cl                                                                         H   CF.sub.3                                                                              OCH.sub.3                                            H     CH.sub.2 Cl                                                                          H   CH.sub.2 F                                                                            OCH.sub.3                                            H     CH.sub.2 Cl                                                                          H   CH.sub.2 Cl                                                                           OCH.sub.3                                            H     CH.sub.2 Cl                                                                          H   CH.sub.2 Br                                                                           OCH.sub.3                                            H     CH.sub.2 Cl                                                                          H   F       OCH.sub.3                                            H     CH.sub.2 Cl                                                                          H   I       OCH.sub.3                                            H     CH.sub.2 Cl                                                                          H   OCH.sub.2 CH.sub.2 F                                                                  OCH.sub.3                                            H     CH.sub.2 Cl                                                                          H   OCH.sub.2 CH.sub.2 CF.sub.3                                                           OCH.sub.3                                            H     CH.sub.2 Cl                                                                          H   OCH.sub.2 CHF.sub.2                                                                   CH.sub.3                                             H     CH.sub.2 Cl                                                                          H   OCH.sub.2 CF.sub.3                                                                    CH.sub.3                                             H     CH.sub.2 Cl                                                                          H   Cl      OC.sub.2 H.sub.5                                                                        117-120                                    H     CH.sub.2 Cl                                                                          H   OC.sub.2 H.sub.5                                                                      NHCH.sub.3                                           H     CH.sub.2 Cl                                                                          H   OCH.sub.3                                                                             CH.sub.2 SCH.sub.3                                   H     CH.sub.2 Cl                                                                          H   OCF.sub.2 H                                                                           CH.sub.3                                             H     CH.sub.2 Cl                                                                          H   Cl      OCF.sub.2 H                                          H     CHClCH.sub.3                                                                         H   OCH.sub.3                                                                             OCH.sub.3 139-142                                    H     CHClCH.sub.3                                                                         H   CH.sub.3                                                                              OCH.sub.3 131-133                                    H     CHClCH.sub.3                                                                         H   CH.sub.3                                                                              CH.sub.3                                             H     CHClCH.sub.3                                                                         H   Cl      OCH.sub.3 137-138                                    H     CHClCH.sub.3                                                                         H   Br      OCH.sub.3                                            H     CHClCH.sub.3                                                                         H   CH.sub.3                                                                              H                                                    H     CHClCH.sub.3                                                                         H   OCH.sub.3                                                                             H                                                    H     CHClCH.sub.3                                                                         H   OCH.sub.3                                                                             CH.sub.2 OC.sub.2 H.sub.5                            H     CHClCH.sub.3                                                                         H   OCF.sub.2 H                                                                           OCH.sub.3                                            H     CHClCH.sub.3                                                                         H   OCH.sub.3                                                                             CH(OCH.sub.3).sub.3                                  H     CHClCH.sub.3                                                                         H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                   H     CHClCH.sub.3                                                                         H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                   H     CHClCH.sub.3                                                                         H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                      H     CHClCH.sub.3                                                                         H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                      H     CHClCH.sub.3                                                                         H   OC.sub.2 H.sub.5                                                                      OCH.sub.3                                            H     CHClCH.sub.3                                                                         H   OCH.sub.2 CF.sub.3                                                                    OCH.sub.3                                            H     CHClCH.sub.3                                                                         H   CF.sub.3                                                                              OCH.sub.3                                            H     CHClCH.sub.3                                                                         H   CH.sub.2 F                                                                            OCH.sub.3                                            H     CHClCH.sub.3                                                                         H   CH.sub.2 Cl                                                                           OCH.sub.3                                            H     CHClCH.sub.3                                                                         H   CH.sub.2 Br                                                                           OCH.sub.3                                            H     CHClCH.sub.3                                                                         H   F       OCH.sub.3                                            H     CHClCH.sub.3                                                                         H   I       OCH.sub.3                                            H     CHClCH.sub.3                                                                         H   OCH.sub.2 CH.sub.2 F                                                                  OCH.sub.3                                            H     CHClCH.sub.3                                                                         H   OCH.sub.2 CH.sub.2 CF.sub.3                                                           OCH.sub.3                                            H     CHClCH.sub.3                                                                         H   OCH.sub.2 CHF.sub.2                                                                   CH.sub.3                                             H     CHClCH.sub.3                                                                         H   OCH.sub.2 CF.sub.3                                                                    CH.sub.3                                             H     CHClCH.sub.3                                                                         H   Cl      OC.sub. 2 H.sub.5                                    H     CHClCH.sub.3                                                                         H   OC.sub.2 H.sub.5                                                                      NHCH.sub.3                                           H     CHClCH.sub.3                                                                         H   OCH.sub.3                                                                             CH.sub.2 SCH.sub.3                                   H     CHClCH.sub.3                                                                         H   OCF.sub.2 H                                                                           CH.sub.3                                             H     CHClCH.sub.3                                                                         H   Cl      OCF.sub.2 H                                          H     CH.sub.2 BR                                                                          H   OCH.sub.3                                                                             OCH.sub.3                                            H     CH.sub.2 BR                                                                          H   CH.sub.3                                                                              OCH.sub.3                                            H     CH.sub.2 BR                                                                          H   CH.sub.3                                                                              CH.sub.3                                             H     CH.sub.2 BR                                                                          H   Cl      OCH.sub.3                                            H     CH.sub.2 BR                                                                          H   Br      OCH.sub.3                                            H     CH.sub.2 BR                                                                          H   CH.sub.3                                                                              H                                                    H     CH.sub.2 BR                                                                          H   OCH.sub.3                                                                             H                                                    H     CH.sub.2 BR                                                                          H   OCH.sub.3                                                                             CH.sub.2 OC.sub.2 H.sub.5                            H     CH.sub.2 BR                                                                          H   OCF.sub.2 H                                                                           OCH.sub.3                                            H     CH.sub.2 BR                                                                          H   OCH.sub.3                                                                             CH(OCH.sub.3).sub.2                                  H     CH.sub.2 BR                                                                          H   CH.sub.3                                                                              OC.sub.2 H.sub.5                                     H     CH.sub.2 BR                                                                          H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                   H     CH.sub.2 BR                                                                          H   OCH.sub.3                                                                             CH.sub.2 OCH.sub.3                                   H     CH.sub.2 BR                                                                          H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                      H     CH.sub.2 BR                                                                          H   OCH.sub.2 CF.sub.3                                                                    OCH.sub.3                                            H     CH.sub.2 BR                                                                          H   OC.sub.2 H.sub.5                                                                      OCH.sub.3                                            H     CH.sub.2 BR                                                                          H   CF.sub.3                                                                              OCH.sub.3                                            H     CH.sub.2 BR                                                                          H   CH.sub.2 F                                                                            OCH.sub.3                                            H     CH.sub.2 BR                                                                          H   CH.sub.2 Cl                                                                           OCH.sub.3                                            H     CH.sub.2 BR                                                                          H   CH.sub.2 Br                                                                           OCH.sub.3                                            H     CH.sub.2 BR                                                                          H   F       OCH.sub.3                                            H     CH.sub.2 BR                                                                          H   I       OCH.sub.3                                            H     CH.sub.2 BR                                                                          H   OCH.sub.2 CH.sub.2 F                                                                  OCH.sub.3                                            H     CH.sub.2 BR                                                                          H   OCH.sub.2 CH.sub.2 CF.sub.3                                                           OCH.sub.3                                            H     CH.sub.2 BR                                                                          H   OCH.sub.2 CHF.sub.2                                                                   CH.sub.3                                             H     CH.sub.2 BR                                                                          H   OCH.sub.2 CF.sub.3                                                                    CH.sub.3                                             H     CH.sub.2 BR                                                                          H   Cl      OC.sub.2 H.sub.5                                     H     CH.sub.2 BR                                                                          H   OC.sub.2 H.sub.5                                                                      NHCH.sub.3                                           H     CH.sub.2 BR                                                                          H   OCH.sub.3                                                                             CH.sub.2 SCH.sub.3                                   H     CH.sub.2 BR                                                                          H   OCF.sub.2 H                                                                           CH.sub.3                                             H     CH.sub.2 BR                                                                          H   Cl      OCF.sub.2 H                                          H     CHF.sub.2                                                                            H   OCH.sub.3                                                                             OCH.sub.3                                            H     CHF.sub.2                                                                            H   CH.sub.3                                                                              OCH.sub.3                                            H     CHF.sub.2                                                                            H   CH.sub.3                                                                              CH.sub.3                                             H     CHF.sub.2                                                                            H   Cl      OCH.sub.3                                            H     CHF.sub.2                                                                            H   Br      OCH.sub.3                                            H     CHF.sub.2                                                                            H   CH.sub.3                                                                              H                                                    H     CHF.sub.2                                                                            H   OCH.sub.3                                                                             H                                                    H     CHF.sub.2                                                                            H   OCH.sub.3                                                                             CH.sub.2 OC.sub.2 H.sub.5                            H     CHF.sub.2                                                                            H   OCF.sub.2 H                                                                           OCH.sub.3                                            H     CHF.sub.2                                                                            H   OCH.sub.3                                                                             CH(OCH.sub.3).sub.2                                  H     CHF.sub.2                                                                            H   CH.sub.3                                                                              OC.sub.2 H.sub.5                                     H     CHF.sub.2                                                                            H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                   H     CHF.sub.2                                                                            H   OCH.sub.3                                                                             CH.sub.2 OCH.sub.3                                   H     CHF.sub.2                                                                            H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                      H     CHF.sub.2                                                                            H   OC.sub.2 H.sub.5                                                                      OCH.sub.3                                            H     CHF.sub.2                                                                            H   OCH.sub.2 CF.sub.3                                                                    OCH.sub.3                                            H     CHF.sub.2                                                                            H   CF.sub.3                                                                              OCH.sub.3                                            H     CHF.sub.2                                                                            H   CH.sub.2 F                                                                            OCH.sub.3                                            H     CHF.sub.2                                                                            H   CH.sub.2 Cl                                                                           OCH.sub.3                                            H     CHF.sub.2                                                                            H   CH.sub.2 Br                                                                           OCH.sub.3                                            H     CHF.sub.2                                                                            H   F       OCH.sub.3                                            H     CHF.sub.2                                                                            H   I       OCH.sub.3                                            H     CHF.sub.2                                                                            H   OCH.sub.2 CH.sub.2 F                                                                  OCH.sub.3                                            H     CHF.sub.2                                                                            H   OCH.sub.2 CH.sub.2 CF.sub.3                                                           OCH.sub.3                                            H     CHF.sub.2                                                                            H   OCH.sub.2 CF.sub.3                                                                    CH.sub.3                                             H     CHF.sub.2                                                                            H   OCH.sub.2 CHF.sub.2                                                                   CH.sub.3                                             H     CHF.sub.2                                                                            H   Cl      OC.sub.2 H.sub.5                                     H     CHF.sub.2                                                                            H   OC.sub.2 H.sub.5                                                                      NHCH.sub.3                                           H     CHF.sub.2                                                                            H   OCH.sub.3                                                                             CH.sub.2 SCH.sub.3                                   H     CHF.sub.2                                                                            H   OCF.sub.2 H                                                                           CH.sub.3                                             H     CHF.sub.2                                                                            H   Cl      OCF.sub.2 H                                          H     CHFCl  H   OCH.sub.3                                                                             OCH.sub.3                                            H     CHFCl  H   CH.sub.3                                                                              OCH.sub.3                                            H     CHFCl  H   CH.sub.3                                                                              CH.sub.3                                             H     CHFCl  H   Cl      OCH.sub.3                                            H     CHFCl  H   Br      OCH.sub.3                                            H     CHFCl  H   CH.sub.3                                                                              H                                                    H     CHFCl  H   OCH.sub.3                                                                             H                                                    H     CHFCl  H   OCH.sub.3                                                                             CH.sub.2 OC.sub.2 H.sub.5                            H     CHFCl  H   OCF.sub.2 H                                                                           OCH.sub.3                                            H     CHFCl  H   OCH.sub.3                                                                             CH(OCH.sub.3).sub.2                                  H     CHFCl  H   CH.sub.3                                                                              OC.sub.2 H.sub.5                                     H     CHFCl  H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                   H     CHFCl  H   OCH.sub.3                                                                             CH.sub.2 OCH.sub.3                                   H     CHFCl  H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                      H     CHFCl  H   OC.sub.2 H.sub.5                                                                      OCH.sub.3                                            H     CHFCl  H   OCH.sub.2 CF.sub.3                                                                    OCH.sub.3                                            H     CHFCl  H   CF.sub.3                                                                              OCH.sub.3                                            H     CHFCl  H   CH.sub.2 F                                                                            OCH.sub.3                                            H     CHFCl  H   CH.sub.2 Cl                                                                           OCH.sub.3                                            H     CHFCl  H   CH.sub.2 Br                                                                           OCH.sub.3                                            H     CHFCl  H   F       OCH.sub.3                                            H     CHFCl  H   I       OCH.sub.3                                            H     CHFCl  H   OCH.sub.2 CH.sub.2 F                                                                  OCH.sub.3                                            H     CHFCl  H   OCH.sub.2 CH.sub.2 CF.sub.3                                                           OCH.sub.3                                            H     CHFCl  H   OCH.sub.2 CHF.sub.2                                                                   CH.sub.3                                             H     CHFCl  H   OCH.sub.2 CF.sub.3                                                                    CH.sub.3                                             H     CHFCl  H   Cl      OC.sub.2 H.sub.5                                     H     CHFCl  H   OC.sub.2 H.sub.5                                                                      NHCH.sub.3                                           H     CHFCl  H   OCH.sub.3                                                                             CH.sub.2 SCH.sub.3                                   H     CHFCl  H   OCF.sub.2 H                                                                           CH.sub.3                                             H     CHFCl  H   Cl      OCF.sub.2 H                                          H     CHFCl  H   n-C.sub.3 F.sub.7                                                                     OCH.sub.3                                            H     CHFCl  H   OCH.sub.3                                                                             NHCH.sub.3                                           H     CHFCl  H   OCH.sub.3                                                                             N(CH.sub.3).sub.2                                    H     CHFCl  H   OCH.sub.3                                                                             cyclopropyl                                          H     CHFCl  H   OCH.sub.3                                                                             OCH.sub.2 CH.sub.2 OCH.sub.3                         H     CHFCl  H   OC.sub.2 H.sub.5                                                                      CH.sub.2 SCH.sub.3                                   H     CHFCl  H   OCH.sub.3                                                                             CH(SCH.sub.3)OC.sub.2 H.sub.5                        H     CHFCl  H   OCH.sub.3                                                                             CH(SC.sub.2 H.sub.5).sub.2                           H     CHFCl  H   OCH.sub.3                                                                             1,3-dioxolan-2-yl                                    H     CHFCl  H   OCH.sub.3                                                                             N(OCH.sub.3)CH.sub.3                                 H     CHFCl  H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                      H     CHFCl  H   OCH.sub.3                                                                             CF.sub.3                                             6-F   CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.3                                            6-Cl  CH.sub. 2 F                                                                          H   OCH.sub.3                                                                             OCH.sub.3                                            6-Cl  CH.sub.2 Cl                                                                          H   OCH.sub.3                                                                             OCH.sub.3                                            6-Cl  CH.sub.2 F                                                                           H   CH.sub.3                                                                              OCH.sub.3                                            6-Cl  CH.sub.2 F                                                                           H   CH.sub.3                                                                              CH.sub.3                                             6-Cl  CH.sub.2 F                                                                           H   Cl      OCH.sub.3                                            6-Br  CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.3                                            6-CH.sub.2 CN                                                                       CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.3                                            6-OCH.sub.3                                                                         CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.3                                            6-SCH.sub.3                                                                         CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.3                                            6-OCF.sub.2 H                                                                       CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.3                                            H     CH.sub.2 F                                                                           CH.sub.3                                                                          OCH.sub.3                                                                             OCH.sub.3                                            H     CH.sub.2 F                                                                           CH.sub.3                                                                          CH.sub.3                                                                              OCH.sub.3                                            H     CH.sub.2 Cl                                                                          CH.sub.3                                                                          OCH.sub.3                                                                             OCH.sub.3                                            H     CHF.sub.2                                                                            CH.sub.3                                                                          OCH.sub.3                                                                             OCH.sub.3                                            H     CH.sub.2 Br                                                                          CH.sub.3                                                                          OCH.sub.3                                                                             OCH.sub.3                                            6-Cl  CH.sub.2 Cl                                                                          CH.sub.3                                                                          OCH.sub.3                                                                             OCH.sub.3                                            __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________     ##STR48##                                                                    R.sup.1                                                                              R.sup.2                                                                              R.sup.3                                                                           X       Y        mp (°C.)                            __________________________________________________________________________    H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.3                                                                              162-164                                    H      CH.sub.2 F                                                                           H   CH.sub.3                                                                              OCH.sub.3                                                                              147-149                                    H      CH.sub.2 F                                                                           H   CH.sub.3                                                                              OCH.sub.3                                                                              155-151                                    H      CH.sub.2 F                                                                           H   Cl      OCH.sub.3                                                                              125-128                                    H      CH.sub.2 F                                                                           H   Br      OCH.sub.3                                           H      CH.sub.2 F                                                                           H   H       CH.sub.3                                            H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             H                                                   H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             CH.sub.2 OC.sub.2 H.sub.5                           H      CH.sub.2 F                                                                           H   OCF.sub.2 H                                                                           OCH.sub.3                                           H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             CH(OCH.sub.3).sub. 2                                H      CH.sub.2 F                                                                           H   CH.sub.3                                                                              OC.sub.2 H.sub.5                                    H      CH.sub.2 F                                                                           H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                  H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             CH.sub.2 OCH.sub.3                                  H      CH.sub.2 F                                                                           H   C.sub.2 H.sub.5                                                                       OCH.sub.3                                           H      CH.sub.2 F                                                                           H   OC.sub.2 H.sub.5                                                                      OCH.sub.3                                           H      CH.sub.2 F                                                                           H   OCH.sub.2 CF.sub.3                                                                    OCH.sub.3                                           H      CH.sub.2 F                                                                           H   CF.sub.3                                                                              OCH.sub.3                                           H      CH.sub.2 F                                                                           H   CH.sub.2 F                                                                            OCH.sub.3                                           H      CH.sub.2 F                                                                           H   CH.sub.2 Cl                                                                           OCH.sub.3                                           H      CH.sub.2 F                                                                           H   CF.sub.2 Br                                                                           OCH.sub.3                                           H      CH.sub.2 F                                                                           H   F       OCH.sub.3                                           H      CH.sub.2 F                                                                           H   I       OCH.sub.3                                           H      CH.sub.2 F                                                                           H   OCH.sub.2 CH.sub.2 F                                                                  OCH.sub.3                                           H      CH.sub.2 F                                                                           H   OCH.sub.2 CH.sub.2 CF.sub.3                                                           OCH.sub.3                                           H      CH.sub.2 F                                                                           H   OCH.sub.2 CHF.sub.2                                                                   CH.sub.3                                            H      CH.sub.2 F                                                                           H   OCH.sub.2 CF.sub.3                                                                    CH.sub.3                                            H      CH.sub.2 F                                                                           H   Cl      OC.sub.2 H.sub.5                                                                       115-117                                    H      CH.sub.2 F                                                                           H   OC.sub.2 H.sub.5                                                                      NHCH.sub.3                                          H      CH.sub.2 F                                                                           H   OC.sub.2 H.sub. 5                                                                     CH.sub.2 SCH.sub.3                                  H      CH.sub.2 F                                                                           H   OCF.sub.2 H                                                                           CH.sub.3                                            H      CH.sub.2 F                                                                           H   Cl      OCF.sub.2 H                                         H      CH.sub.2 F                                                                           H   NH.sub.2                                                                              OC.sub.2 H.sub.5                                    H      CH.sub.2 F                                                                           H   n-C.sub.3 H.sub.7                                                                     OCH.sub.3                                           H      CH.sub.2 F                                                                           H   NHCH.sub.3                                                                            OCH.sub.3                                           H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             SCH.sub.3                                           H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             SCF.sub.2 H                                         H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.2 CCH                                       H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.2 CHCH.sub.2                                H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             CCH                                                 H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             N(CH.sub.3).sub.2                                   H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             cyclopropyl                                         H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             NH.sub.2                                            H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             CF.sub.3                                            H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.2 CH.sub.2 OCH.sub.3                        H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             CH.sub.2 SCH.sub.3                                  H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             CHO                                                 H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             COCH.sub.3                                          H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             CH(SCH.sub.3)OC.sub.2 H.sub.5                       H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             C(CH.sub.3)(SCH.sub.3).sub.2                        H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             C(SC.sub.2 H.sub.5).sub.2                           H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             1,3-dioxolan-2-yl                                   H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             2-methyl-1,3-                                                                 oxathiolan-2yl                                      H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             1,3-oxathian-2-yl                                   H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             2-methyl-1,3-                                                                 dithian-2-yl                                        H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             4-methyl-1,3-                                                                 dioxolan-2-yl                                       H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             2-4-dimethyl-1,3-                                                             dithiolan-2-yl                                      H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             N(OCH.sub.3)(CH.sub.3)                              H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             CCCH.sub.3                                          H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                     H      CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCF.sub.2 Br                                        H      CHFCH.sub.3                                                                          H   OCH.sub.3                                                                             OCH.sub.3                                                                              137-139                                    H      CHFCH.sub.3                                                                          H   CH.sub.3                                                                              OCH.sub.3                                           H      CHFCH.sub.3                                                                          H   CH.sub.3                                                                              CH.sub.3                                            H      CHFCH.sub.3                                                                          H   Cl      OCH.sub.3                                           H      CHFCH.sub.3                                                                          H   Br      OCH.sub. 3                                          H      CHFCH.sub.3                                                                          H   CH.sub.3                                                                              H                                                   H      CHFCH.sub.3                                                                          H   OCH.sub.3                                                                             H                                                   H      CHFCH.sub.3                                                                          H   OCH.sub.3                                                                             CH.sub.2 OC.sub.2 H.sub.5                           H      CHFCH.sub.3                                                                          H   OCF.sub.2 H                                                                           OCH.sub.3                                           H      CHFCH.sub.3                                                                          H   OCH.sub.3                                                                             CH(OCH.sub.3).sub.2                                 H      CHFCH.sub.3                                                                          H   CH.sub.3                                                                              OC.sub.2 H.sub.5                                    H      CHFCH.sub.3                                                                          H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                  H      CHFCH.sub.3                                                                          H   OCH.sub.3                                                                             CH.sub.2 OCH.sub.3                                  H      CHFCH.sub.3                                                                          H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                     H      CHFCH.sub.3                                                                          H   OC.sub.2 H.sub.5                                                                      OCH.sub.3                                           H      CHFCH.sub.3                                                                          H   OCH.sub.2 CF.sub.3                                                                    OCH.sub.3                                           H      CHFCH.sub.3                                                                          H   CF.sub.3                                                                              OCH.sub.3                                           H      CHFCH.sub.3                                                                          H   CH.sub.2 F                                                                            OCH.sub.3                                           H      CHFCH.sub.3                                                                          H   CH.sub.2 Cl                                                                           OCH.sub.3                                           H      CHFCH.sub.3                                                                          H   CH.sub.2 Br                                                                           OCH.sub.3                                           H      CHFCH.sub.3                                                                          H   F       OCH.sub.3                                           H      CHFCH.sub.3                                                                          H   I       OCH.sub.3                                           H      CHFCH.sub.3                                                                          H   OCH.sub.2 CH.sub.2 F                                                                  OCH.sub.3                                           H      CHFCH.sub.3                                                                          H   OCH.sub.2 CH.sub.2 CF.sub.3                                                           OCH.sub.3                                           H      CHFCH.sub.3                                                                          H   OCH.sub.2 CHF.sub.2                                                                   CH.sub.3                                            H      CHFCH.sub.3                                                                          H   OCH.sub.2 CF.sub.3                                                                    CH.sub.3                                            H      CHFCH.sub. 3                                                                         H   Cl      OC.sub.2 H.sub.5                                    H      CHFCH.sub.3                                                                          H   OC.sub.2 H.sub.5                                                                      NHCH.sub.3                                          H      CHFCH.sub.3                                                                          H   OCH.sub.3                                                                             CH.sub.2 SCH.sub.3                                  H      CHFCH.sub.3                                                                          H   OCF.sub.2 H                                                                           CH.sub.3                                            H      CHFCH.sub.3                                                                          H   Cl      OCF.sub.2 H                                         H      CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.3                                                                             OCH.sub.3                                           H      CH.sub.2 CH.sub.2 F                                                                  H   CH.sub.3                                                                              OCH.sub.3                                           H      CH.sub.2 CH.sub.2 F                                                                  H   CH.sub.3                                                                              CH.sub.3                                            H      CH.sub.2 CH.sub.2 F                                                                  H   Cl      OCH.sub.3                                           H      CH.sub.2 CH.sub.2 F                                                                  H   Br      OCH.sub.3                                           H      CH.sub.2 CH.sub.2 F                                                                  H   CH.sub.3                                                                              H                                                   H      CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.3                                                                             H                                                   H      CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.3                                                                             CH.sub.2 OC.sub.2 H.sub.5                           H      CH.sub.2 CH.sub.2 F                                                                  H   OCF.sub.2 H                                                                           OCH.sub.3                                           H      CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.3                                                                             CH(OCH.sub.3).sub.2                                 H      CH.sub.2 CH.sub.2 F                                                                  H   CH.sub.3                                                                              OC.sub.2 H.sub.5                                    H      CH.sub.2 CH.sub.2 F                                                                  H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                  H      CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.3                                                                             CH.sub.2 OCH.sub.3                                  H      CH.sub.2 CH.sub. 2 F                                                                 H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                     H      CH.sub.2 CH.sub.2 F                                                                  H   OC.sub.2 H.sub.5                                                                      OCH.sub.3                                           H      CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.2 CF.sub.3                                                                    OCH.sub.3                                           H      CH.sub.2 CH.sub.2 F                                                                  H   CF.sub.3                                                                              OCH.sub.3                                           H      CH.sub.2 CH.sub.2 F                                                                  H   CH.sub.2 F                                                                            OCH.sub.3                                           H      CH.sub.2 CH.sub.2 F                                                                  H   CH.sub.2 Cl                                                                           OCH.sub.3                                           H      CH.sub.2 CH.sub.2 F                                                                  H   CH.sub.2 Br                                                                           OCH.sub.3                                           H      CH.sub.2 CH.sub.2 F                                                                  H   F       OCH.sub.3                                           H      CH.sub.2 CH.sub.2 F                                                                  H   I       OCH.sub.3                                           H      CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.2 CH.sub.2 F                                                                  OCH.sub.3                                           H      CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.2 CH.sub.2 CF.sub.3                                                           OCH.sub.3                                           H      CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.2 CHF.sub.2                                                                   CH.sub.3                                            H      CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.2 CF.sub.3                                                                    CH.sub.3                                            H      CH.sub.2 CH.sub.2 F                                                                  H   Cl      OC.sub.2 H.sub.5                                    H      CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.2 H.sub.5                                                                     NHCH.sub.3                                          H      CH.sub.2 CH.sub.2 F                                                                  H   OCH.sub.3                                                                             CH.sub.2 SCH.sub.3                                  H      CH.sub.2 CH.sub.2 F                                                                  H   OCF.sub.2 H                                                                           CH.sub.3                                            H      CH.sub.2 CH.sub.2 F                                                                  H   Cl      OCF.sub.2 H                                         H      CH.sub.2 Cl                                                                          H   OCH.sub.3                                                                             OCH.sub.3                                           H      CH.sub.2 Cl                                                                          H   CH.sub.3                                                                              OCH.sub.3                                           H      CH.sub.2 Cl                                                                          H   CH.sub.3                                                                              CH.sub.3                                            H      CH.sub.2 Cl                                                                          H   Cl      OCH.sub.3                                           H      CH.sub.2 Cl                                                                          H   Br      OCH.sub.3                                           H      CH.sub.2 Cl                                                                          H   CH.sub.3                                                                              H                                                   H      CH.sub.2 Cl                                                                          H   OCH.sub.3                                                                             H                                                   H      CH.sub.2 Cl                                                                          H   OCH.sub.3                                                                             CH.sub.2 OC.sub.2 H.sub.5                           H      CH.sub.2 Cl                                                                          H   OCF.sub.2 H                                                                           OCH.sub.3                                           H      CH.sub.2 Cl                                                                          H   OCH.sub.3                                                                             CH(OCH.sub.3).sub.2                                 H      CH.sub.2 Cl                                                                          H   CH.sub.3                                                                              OC.sub.2 H.sub.5                                    H      CH.sub.2 Cl                                                                          H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                  H      CH.sub.2 Cl                                                                          H   OCH.sub.3                                                                             CH.sub.2 OCH.sub.3                                  H      CH.sub.2 Cl                                                                          H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                     H      CH.sub.2 Cl                                                                          H   OC.sub.2 H.sub.5                                                                      OCH.sub.3                                           H      CH.sub.2 Cl                                                                          H   OCH.sub.2 CF.sub.3                                                                    OCH.sub.3                                           H      CH.sub.2 Cl                                                                          H   CF.sub.3                                                                              OCH.sub.3                                           H      CH.sub.2 Cl                                                                          H   CH.sub.2 F                                                                            OCH.sub.3                                           H      CH.sub.2 Cl                                                                          H   CH.sub.2 Cl                                                                           OCH.sub.3                                           H      CH.sub.2 Cl                                                                          H   CH.sub.2 Br                                                                           OCH.sub.3                                           H      CH.sub.2 Cl                                                                          H   F       OCH.sub.3                                           H      CH.sub.2 Cl                                                                          H   I       OCH.sub.3                                           H      CH.sub.2 Cl                                                                          H   OCH.sub.2 CH.sub.2 F                                                                  OCH.sub.3                                           H      CH.sub.2 Cl                                                                          H   OCH.sub.2 CH.sub.2 CF.sub.3                                                           OCH.sub.3                                           H      CH.sub.2 Cl                                                                          H   OCH.sub.2 CHF.sub.2                                                                   CH.sub.3                                            H      CH.sub.2 Cl                                                                          H   OCH.sub.2 CF.sub.3                                                                    CH.sub.3                                            H      CH.sub.2 Cl                                                                          H   Cl      OC.sub.2 H.sub.5                                    H      CH.sub.2 Cl                                                                          H   OC.sub.2 H.sub.5                                                                      NHCH.sub.3                                          H      CH.sub.2 Cl                                                                          H   OCH.sub.3                                                                             CH.sub.2 SCH.sub.3                                  H      CH.sub.2 Cl                                                                          H   OCF.sub.2 H                                                                           CH.sub.3                                            H      CH.sub.2 Cl                                                                          H   Cl      OCF.sub.2 H                                         H      CHClCH.sub.3                                                                         H   OCH.sub.3                                                                             OCH.sub.3                                           H      CHClCH.sub.3                                                                         H   CH.sub.3                                                                              OCH.sub.3                                           H      CHClCH.sub.3                                                                         H   CH.sub.3                                                                              CH.sub.3                                            H      CHClCH.sub.3                                                                         H   Cl      OCH.sub.3                                           H      CHClCH.sub.3                                                                         H   Br      OCH.sub.3                                           H      CHClCH.sub.3                                                                         H   CH.sub.3                                                                              H                                                   H      CHClCH.sub.3                                                                         H   OCH.sub.3                                                                             H                                                   H      CHClCH.sub.3                                                                         H   OCH.sub.3                                                                             CH.sub.2 OC.sub.2 H.sub.5                           H      CHClCH.sub.3                                                                         H   OCF.sub.2 H                                                                           OCH.sub.3                                           H      CHClCH.sub.3                                                                         H   OCH.sub.3                                                                             CH(OCH.sub.3).sub.2                                 H      CHClCH.sub.3                                                                         H   CH.sub.3                                                                              OC.sub.2 H.sub.5                                    H      CHClCH.sub.3                                                                         H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                  H      CHClCH.sub.3                                                                         H   OCH.sub.3                                                                             CH.sub.2 OCH.sub.3                                  H      CHClCH.sub.3                                                                         H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                     H      CHClCH.sub.3                                                                         H   OC.sub.2 H.sub.5                                                                      OCH.sub.3                                           H      CHClCH.sub.3                                                                         H   OCH.sub.2 CF.sub.3                                                                    OCH.sub.3                                           H      CHClCH.sub.3                                                                         H   CF.sub.3                                                                              OCH.sub.3                                           H      CHClCH.sub.3                                                                         H   CH.sub.2 F                                                                            OCH.sub.3                                           H      CHClCH.sub.3                                                                         H   CH.sub.2 Cl                                                                           OCH.sub.3                                           H      CHClCH.sub.3                                                                         H   CH.sub.2 Br                                                                           OCH.sub.3                                           H      CHClCH.sub.3                                                                         H   F       OCH.sub.3                                           H      CHClCH.sub.3                                                                         H   I       OCH.sub.3                                           H      CHClCH.sub.3                                                                         H   OCH.sub.2 CH.sub.2 F                                                                  OCH.sub.3                                           H      CHClCH.sub.3                                                                         H   OCH.sub.2 CH.sub.2 CF.sub.3                                                           OCH.sub.3                                           H      CHClCH.sub.3                                                                         H   OCH.sub.2 CHF.sub.2                                                                   CH.sub.3                                            H      CHClCH.sub.3                                                                         H   OCH.sub.2 CF.sub.3                                                                    CH.sub.3                                            H      CHClCH.sub.3                                                                         H   Cl      OC.sub.2 H.sub.5                                    H      CHClCH.sub.3                                                                         H   OC.sub.2 H.sub.5                                                                      NHCH.sub.3                                          H      CHClCH.sub.3                                                                         H   OCH.sub.3                                                                             CH.sub.2 SCH.sub.3                                  H      CHClCH.sub.3                                                                         H   OCF.sub.2 H                                                                           CH.sub.3                                            H      CHClCH.sub.3                                                                         H   Cl      OCF.sub.2 H                                         H      CH.sub.2 Br                                                                          H   OCH.sub.3                                                                             OCH.sub.3                                           H      CH.sub.2 Br                                                                          H   CH.sub.3                                                                              OCH.sub.3                                           H      CH.sub.2 Br                                                                          H   CH.sub.3                                                                              CH.sub.3                                            H      CH.sub.2 Br                                                                          H   Cl      OCH.sub.3                                           H      CH.sub.2 Br                                                                          H   Br      OCH.sub.3                                           H      CH.sub.2 Br                                                                          H   CH.sub.3                                                                              H                                                   H      CH.sub.2 Br                                                                          H   OCH.sub.3                                                                             H                                                   H      CH.sub.2 Br                                                                          H   OCH.sub.3                                                                             CH.sub.2 OC.sub.2 H.sub.5                           H      CH.sub.2 Br                                                                          H   OCF.sub.2 H                                                                           OCH.sub.3                                           H      CH.sub.2 Br                                                                          H   OCH.sub.3                                                                             CH(OCH.sub.3).sub.2                                 H      CH.sub.2 Br                                                                          H   CH.sub.3                                                                              OC.sub.2 H.sub.5                                    H      CH.sub.2 Br                                                                          H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                  H      CH.sub.2 Br                                                                          H   OCH.sub.3                                                                             CH.sub.2 OCH.sub.3                                  H      CH.sub.2 Br                                                                          H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                     H      CH.sub.2 Br                                                                          H   OC.sub.2 H.sub.5                                                                      OCH.sub.3                                           H      CH.sub.2 Br                                                                          H   OCH.sub.2 CF.sub.3                                                                    OCH.sub.3                                           H      CH.sub.2 Br                                                                          H   CF.sub.3                                                                              OCH.sub.3                                           H      CH.sub.2 Br                                                                          H   CH.sub.2 F                                                                            OCH.sub.3                                           H      CH.sub.2 Br                                                                          H   CH.sub.2 Cl                                                                           OCH.sub.3                                           H      CH.sub.2 Br                                                                          H   CH.sub.2 Br                                                                           OCH.sub.3                                           H      CH.sub.2 Br                                                                          H   F       OCH.sub.3                                           H      CH.sub.2 Br                                                                          H   I       OCH.sub.3                                           H      CH.sub.2 Br                                                                          H   OCH.sub.2 CH.sub.2 F                                                                  OCH.sub.3                                           H      CH.sub.2 Br                                                                          H   OCH.sub.2 CH.sub.2 CF.sub.3                                                           OCH.sub.3                                           H      CH.sub.2 Br                                                                          H   OCH.sub.2 CHF.sub.2                                                                   CH.sub.3                                            H      CH.sub.2 Br                                                                          H   OCH.sub.2 CF.sub.3                                                                    CH.sub.3                                            H      CH.sub.2 Br                                                                          H   Cl      OC.sub.2 H.sub.5                                    H      CH.sub.2 Br                                                                          H   OC.sub.2 H.sub.5                                                                      NHCH.sub.3                                          H      CH.sub.2 Br                                                                          H   OCH.sub.3                                                                             CH.sub.2 SCH.sub.3                                  H      CH.sub.2 Br                                                                          H   OCF.sub.2 H                                                                           CH.sub.3                                            H      CH.sub.2 Br                                                                          H   Cl      OCF.sub.2 H                                         H      CHF.sub.2                                                                            H   OCH.sub.3                                                                             OCH.sub.3                                           H      CHF.sub.2                                                                            H   CH.sub.3                                                                              OCH.sub.3                                           H      CHF.sub.2                                                                            H   CH.sub.3                                                                              CH.sub.3                                            H      CHF.sub.2                                                                            H   Cl      OCH.sub.3                                           H      CHF.sub.2                                                                            H   Br      OCH.sub.3                                           H      CHF.sub.2                                                                            H   CH.sub.3                                                                              H                                                   H      CHF.sub.2                                                                            H   OCH.sub.3                                                                             H                                                   H      CHF.sub.2                                                                            H   OCH.sub.3                                                                             CH.sub.2 OC.sub.2 H.sub.5                           H      CHF.sub.2                                                                            H   OCF.sub.2 H                                                                           OCH.sub.3                                           H      CHF.sub.2                                                                            H   OCH.sub.3                                                                             CH(OCH.sub.3).sub.2                                 H      CHF.sub.2                                                                            H   CH.sub.3                                                                              OC.sub.2 H.sub.5                                    H      CHF.sub.2                                                                            H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                  H      CHF.sub.2                                                                            H   OCH.sub.3                                                                             CH.sub.2 OCH.sub.3                                  H      CHF.sub.2                                                                            H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                     H      CHF.sub.2                                                                            H   OC.sub.2 H.sub.5                                                                      OCH.sub.3                                           H      CHF.sub.2                                                                            H   OCH.sub.2 CF.sub.3                                                                    OCH.sub.3                                           H      CHF.sub.2                                                                            H   CF.sub.3                                                                              OCH.sub.3                                           H      CHF.sub.2                                                                            H   CH.sub.2 F                                                                            OCH.sub.3                                           H      CHF.sub.2                                                                            H   CH.sub.2 Cl                                                                           OCH.sub.3                                           H      CHF.sub.2                                                                            H   CH.sub.2 Br                                                                           OCH.sub.3                                           H      CHF.sub.2                                                                            H   F       OCH.sub.3                                           H      CHF.sub.2                                                                            H   I       OCH.sub.3                                           H      CHF.sub.2                                                                            H   OCH.sub.2 CH.sub.2 F                                                                  OCH.sub.3                                           H      CHF.sub.2                                                                            H   OCH.sub.2 CH.sub.2 CF.sub.3                                                           OCH.sub.3                                           H      CHF.sub.2                                                                            H   OCH.sub.2 CF.sub.3                                                                    CH.sub.3                                            H      CHF.sub.2                                                                            H   OCH.sub.2 CHF.sub.2                                                                   CH.sub.3                                            H      CHF.sub.2                                                                            H   Cl      OC.sub.2 H.sub.5                                    H      CHF.sub.2                                                                            H   OC.sub.2 H.sub.5                                                                      NHCH.sub.3                                          H      CHF.sub.2                                                                            H   OCH.sub.3                                                                             CH.sub.2 SCH.sub.3                                  H      CHF.sub.2                                                                            H   OCF.sub.2 H                                                                           CH.sub.3                                            H      CHF.sub.2                                                                            H   Cl      OCF.sub.2 H                                         H      CHFCl  H   OCH.sub.3                                                                             OCH.sub.3                                           H      CHFCl  H   CH.sub.3                                                                              OCH.sub.3                                           H      CHFCl  H   CH.sub.3                                                                              CH.sub.3                                            H      CHFCl  H   Cl      OCH.sub.3                                           H      CHFCl  H   Br      OCH.sub.3                                           H      CHFCl  H   CH.sub.3                                                                              H                                                   H      CHFCl  H   OCH.sub.3                                                                             H                                                   H      CHFCl  H   OCH.sub.3                                                                             CH.sub.2 OC.sub.2 H.sub.5                           H      CHFCl  H   OCF.sub.2 H                                                                           OCH.sub.3                                           H      CHFCl  H   OCH.sub.3                                                                             CH(OCH.sub.3).sub.2                                 H      CHFCl  H   CH.sub.3                                                                              OC.sub.2 H.sub.5                                    H      CHFCl  H   CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                  H      CHFCl  H   OCH.sub.3                                                                             CH.sub.2 OCH.sub.3                                  H      CHFCl  H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                     H      CHFCl  H   OC.sub.2 H.sub.5                                                                      OCH.sub.3                                           H      CHFCl  H   OCH.sub.2 CF.sub.3                                                                    OCH.sub.3                                           H      CHFCl  H   CF.sub.3                                                                              OCH.sub.3                                           H      CHFCl  H   CH.sub.2 F                                                                            OCH.sub.3                                           H      CHFCl  H   CH.sub.2 Cl                                                                           OCH.sub.3                                           H      CHFCl  H   CH.sub.2 Br                                                                           OCH.sub.3                                           H      CHFCl  H   F       OCH.sub.3                                           H      CHFCl  H   I       OCH.sub.3                                           H      CHFCl  H   OCH.sub.2 CH.sub.2 F                                                                  OCH.sub.3                                           H      CHFCl  H   OCH.sub.2 CH.sub.2 CF.sub.3                                                           OCH.sub.3                                           H      CHFCl  H   OCH.sub.2 CHF.sub.2                                                                   CH.sub.3                                            H      CHFCl  H   OCH.sub.2 CF.sub.3                                                                    CH.sub.3                                            H      CHFCl  H   Cl      OC.sub.2 H.sub.5                                    H      CHFCl  H   OC.sub.2 H.sub.5                                                                      NHCH.sub.3                                          H      CHFCl  H   OCH.sub.3                                                                             CH.sub.2 SCH.sub.3                                  H      CHFCl  H   OCF.sub.2 H                                                                           CH.sub.3                                            H      CHFCl  H   Cl      OCF.sub.2 H                                         H      CHFCl  H   n-C.sub.3 H.sub.7                                                                     OCH.sub.3                                           H      CHFCl  H   OCH.sub.3                                                                             NHCH.sub.3                                          H      CHFCl  H   OCH.sub.3                                                                             N(CH.sub.3).sub.2                                   H      CHFCl  H   OCH.sub.3                                                                             cyclopropyl                                         H      CHFCl  H   OCH.sub.3                                                                             OCH.sub.2 CH.sub.2 OCH.sub.3                        H      CHFCl  H   OC.sub.2 H.sub.5                                                                      CH.sub.2 SCH.sub.3                                  H      CHFCl  H   OCH.sub.3                                                                             CH(SCH.sub.3)OC.sub.2 H.sub.5                       H      CHFCl  H   OCH.sub.3                                                                             CH(SC.sub.2 H.sub.5).sub.2                          H      CHFCl  H   OCH.sub.3                                                                             1,3-dioxolan-2-yl                                   H      CHFCl  H   OCH.sub.3                                                                             N(OCH.sub.3)CH.sub.3                                H      CHFCl  H   OCH.sub.3                                                                             C.sub.2 H.sub.5                                     H      CHFCl  H   OCH.sub.3                                                                             CF.sub.3                                            5-F    CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.3                                           5-Cl   CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.3                                           5-Cl   CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.3                                           5-Cl   CH.sub.2 F                                                                           H   CH.sub.3                                                                              OCH.sub.3                                           5-Cl   CH.sub.2 F                                                                           H   CH.sub.3                                                                              CH.sub.3                                            5-Cl   CH.sub.2 F                                                                           H   Cl      OCH.sub.3                                           5-Br   CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.3                                           5-CH.sub.2 CN                                                                        CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.3                                           5-OCH.sub.3                                                                          CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.3                                           5-SCH.sub.3                                                                          CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.3                                           5-OCF.sub.2 H                                                                        CH.sub.2 F                                                                           H   OCH.sub.3                                                                             OCH.sub.3                                           H      CH.sub.2 F                                                                           CH.sub.3                                                                          OCH.sub.3                                                                             OCH.sub.3                                           H      CH.sub.2 F                                                                           CH.sub.3                                                                          OCH.sub.3                                                                             OCH.sub.3                                           H      CH.sub.2 Cl                                                                          CH.sub.3                                                                          OCH.sub.3                                                                             OCH.sub.3                                           H      CHF.sub.2                                                                            CH.sub.3                                                                          OCH.sub.3                                                                             OCH.sub.3                                           H      CH.sub.2 Br                                                                          CH.sub.3                                                                          OCH.sub.3                                                                             OCH.sub.3                                           4-Cl   CH.sub.2 Cl                                                                          CH.sub.3                                                                          OCH.sub.3                                                                             OCH.sub.3                                           __________________________________________________________________________

                  TABLE 3                                                         ______________________________________                                         ##STR49##                                                                                                              mp                                  R.sup.1                                                                           R.sup.2   R.sup.3                                                                             X         Y           (°C.)                        ______________________________________                                        H   CH.sub.2 F                                                                              H     OCH.sub.3 OCH.sub.3                                       H   CH.sub.2 F                                                                              H     CH.sub.3  OCH.sub.3                                       H   CH.sub.2 F                                                                              H     CH.sub.3  CH.sub.3                                        H   CH.sub.2 F                                                                              H     Cl        OCH.sub.3                                       H   CH.sub.2 F                                                                              H     Br        OCH.sub.3                                       H   CH.sub.2 F                                                                              H     H         CH.sub.3                                        H   CH.sub.2 F                                                                              H     OCH.sub.3 H                                               H   CH.sub.2 F                                                                              H     OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5                       H   CH.sub.2 F                                                                              H     OCF.sub.2 H                                                                             OCH.sub.3                                       H   CH.sub.2 F                                                                              H     OCH.sub.3 CH(OCH.sub.3).sub.2                             H   CH.sub.2 F                                                                              H     CH.sub.3  OC.sub.2 H.sub.5                                H   CH.sub.2 F                                                                              H     CH.sub.3  CH.sub.2 OCH.sub.3                              H   CH.sub.2 F                                                                              H     OCH.sub.3 CH.sub.2 OCH.sub.3                              H   CH.sub.2 F                                                                              H     C.sub.2 H.sub.5                                                                         OCH.sub.3                                       H   CH.sub.2 F                                                                              H     OC.sub.2 H.sub.5                                                                        OCH.sub.3                                       H   CH.sub.2 F                                                                              H     OCH.sub.2 CF.sub.3                                                                      OCH.sub.3                                       H   CH.sub.2 F                                                                              H     CF.sub.3  OCH.sub.3                                       H   CH.sub.2 F                                                                              H     CH.sub.2 F                                                                              OCH.sub.3                                       H   CH.sub.2 F                                                                              H     CH.sub.2 Cl                                                                             OCH.sub.3                                       H   CH.sub.2 F                                                                              H     CH.sub.2 Br                                                                             OCH.sub.3                                       H   CH.sub.2 F                                                                              H     F         OCH.sub.3                                       H   CH.sub.2 F                                                                              H     I         OCH.sub.3                                       H   CH.sub.2 F                                                                              H     OCH.sub.2 CH.sub.2 F                                                                    OCH.sub.3                                       H   CH.sub.2 F                                                                              H     OCH.sub.2 CH.sub.2 CF.sub.3                                                             OCH.sub.3                                       H   CH.sub.2 F                                                                              H     OCH.sub.2 CHF.sub.2                                                                     CH.sub.3                                        H   CH.sub.2 F                                                                              H     OCH.sub.2 CF.sub.3                                                                      CH.sub.3                                        H   CH.sub.2 F                                                                              H     Cl        OC.sub.2 H.sub.5                                H   CH.sub.2 F                                                                              H     OC.sub.2 H.sub.5                                                                        NHCH.sub.3                                      H   CH.sub.2 F                                                                              H     OC.sub.2 H.sub.5                                                                        CH.sub.2 SCH.sub. 3                             H   CH.sub.2 F                                                                              H     OCF.sub.2 H                                                                             CH.sub.3                                        H   CH.sub.2 F                                                                              H     Cl        OCF.sub.2 H                                     H   CH.sub.2 F                                                                              H     NH.sub.2  OC.sub.2 H.sub.5                                H   CH.sub.2 F                                                                              H     n-C.sub.3 H.sub.7                                                                       OCH.sub.3                                       H   CH.sub.2 F                                                                              H     NHCH.sub.3                                                                              OCH.sub.3                                       H   CH.sub.2 F                                                                              H     OCH.sub.3 SCH.sub.3                                       H   CH.sub.2 F                                                                              H     OCH.sub.3 SCF.sub.2 H                                     H   CH.sub.2 F                                                                              H     OCH.sub.3 OCH.sub.2 CCH                                   H   CH.sub.2 F                                                                              H     OCH.sub.3 OCH.sub.2 CHCH.sub.2                            H   CH.sub.2 F                                                                              H     OCH.sub.3 CCH                                             H   CH.sub.2 F                                                                              H     OCH.sub.3 N(CH.sub.3).sub.2                               H   CH.sub.2 F                                                                              H     OCH.sub.3 cyclopropyl                                     H   CH.sub.2 F                                                                              H     OCH.sub.3 NH.sub.2                                        H   CH.sub.2 F                                                                              H     OCH.sub.3 CF.sub.3                                        H   CH.sub.2 F                                                                              H     OCH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3                    H   CH.sub.2 F                                                                              H     OCH.sub.3 CH.sub.2 SCH.sub.3                              H   CH.sub.2 F                                                                              H     OCH.sub.3 CHO                                             H   CH.sub.2 F                                                                              H     OCH.sub.3 COCH.sub.3                                      H   CH.sub.2 F                                                                              H     OCH.sub.3 CH(SCH.sub.3)OC.sub.2 H.sub.5                   H   CH.sub.2 F                                                                              H     OCH.sub.3 C(CH.sub.3)(SCH.sub.3).sub.2                    H   CH.sub.2 F                                                                              H     OCH.sub.3 C(SC.sub.2 H.sub.5).sub.2                       H   CH.sub.2 F                                                                              H     OCH.sub.3 1,3-dioxolan-2-yl                               H   CH.sub.2 F                                                                              H     OCH.sub.3 2-methyl-1,3-                                                                 oxathiolan-2yl                                  H   CH.sub.2 F                                                                              H     OCH.sub.3 1,3-oxathian-2-yl                               H   CH.sub.2 F                                                                              H     OCH.sub.3 2-methyl-1,3-dithian-                                                         2-yl                                            H   CH.sub.2 F                                                                              H     OCH.sub.3 4-methyl-1,3-                                                                 dioxolan-2-yl                                   H   CH.sub.2 F                                                                              H     OCH.sub.3 2-4-dimethyl-1,3-                                                             dithiolan-2-yl                                  H   CH.sub.2 F                                                                              H     OCH.sub.3 N(OCH.sub.3)(CH.sub.3)                          H   CH.sub.2 F                                                                              H     OCH.sub.3 CCCH.sub.3                                      H   CH.sub.2 F                                                                              H     OCH.sub.3 C.sub.2 H.sub.5                                 H   CH.sub.2 F                                                                              H     OCH.sub.3 OCF.sub.2 Br                                    H   CHFCH.sub.3                                                                             H     OCH.sub.3 OC.sub.2 H.sub.5                                H   CHFCH.sub.3                                                                             H     CH.sub.3  OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     CH.sub.3  CH.sub.3                                        H   CHFCH.sub.3                                                                             H     Cl        OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     Br        OCH.sub.3                                       H   CHFCH.sub. 3                                                                            H     CH.sub.3  H                                               H   CHFCH.sub.3                                                                             H     OCH.sub.3 H                                               H   CHFCH.sub.3                                                                             H     OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5                       H   CHFCH.sub.3                                                                             H     OCF.sub.2 H                                                                             OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     OCH.sub.3 CH(OCH.sub.3).sub.2                             H   CHFCH.sub.3                                                                             H     CH.sub.3  OC.sub.2 H.sub.5                                H   CHFCH.sub.3                                                                             H     CH.sub.3  CH.sub.2 OCH.sub.3                              H   CHFCH.sub.3                                                                             H     OCH.sub.3 CH.sub.2 OCH.sub.3                              H   CHFCH.sub.3                                                                             H     OCH.sub.3 C.sub.2 H.sub.5                                 H   CHFCH.sub.3                                                                             H     OC.sub.2 H.sub.5                                                                        OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     OCH.sub.2 CF.sub.3                                                                      OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     CF.sub.3  OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     CH.sub.2 F                                                                              OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     CH.sub.2 Cl                                                                             OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     CH.sub.2 Br                                                                             OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     F         OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     I         OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     OCH.sub.2 CH.sub.2 F                                                                    OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     OCH.sub.2 CH.sub.2 CF.sub.3                                                             OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     OCH.sub.2 CHF.sub.2                                                                     CH.sub.3                                        H   CHFCH.sub.3                                                                             H     OCH.sub.2 CF.sub.3                                                                      CH.sub.3                                        H   CHFCH.sub.3                                                                             H     Cl        OC.sub.2 H.sub.5                                H   CHFCH.sub.3                                                                             H     OC.sub.2 H.sub.5                                                                        NHCH.sub.3                                      H   CHFCH.sub.3                                                                             H     OCH.sub.3 CH.sub.2 SCH.sub.3                              H   CHFCH.sub.3                                                                             H     OCF.sub.2 H                                                                             CH.sub.3                                        H   CHFCH.sub.3                                                                             H     Cl        OCF.sub.2 H                                     H   CH.sub.2 CH.sub.2 F                                                                     H     OCH.sub.3 OCH.sub.3                                       H   CH.sub.2 CH.sub.2 F                                                                     H     CH.sub.3  OCH.sub.3                                       H   CH.sub.2 CH.sub.2 F                                                                     H     CH.sub.3  CH.sub.3                                        H   CH.sub.2 CH.sub.2 F                                                                     H     Cl        OCH.sub.3                                       H   CH.sub.2 CH.sub.2 F                                                                     H     Br        OCH.sub.3                                       H   CH.sub.2 CH.sub.2 F                                                                     H     CH.sub.3  H                                               H   CH.sub.2 CH.sub.2 F                                                                     H     OCH.sub.3 H                                               H   CH.sub.2 CH.sub.2 F                                                                     H     OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5                       H   CH.sub.2 CH.sub.2 F                                                                     H     OCF.sub.2 H                                                                             OCH.sub.3                                       H   CH.sub.2 CH.sub.2 F                                                                     H     OCH.sub.3 CH(OCH.sub.3).sub.2                             H   CH.sub.2 CH.sub.2 F                                                                     H     CH.sub.3  OC.sub.2 H.sub.5                                H   CH.sub.2 CH.sub.2 F                                                                     H     CH.sub.3  CH.sub.2 OCH.sub.3                              H   CH.sub.2 CH.sub.2 F                                                                     H     OCH.sub.3 CH.sub.2 OCH.sub.3                              H   CH.sub.2 CH.sub.2 F                                                                     H     OCH.sub.3 C.sub.2 H.sub.5                                 H   CH.sub.2 CH.sub.2 F                                                                     H     OC.sub.2 H.sub.5                                                                        OCH.sub.3                                       H   CH.sub.2 CH.sub.2 F                                                                     H     OCH.sub.2 CF.sub.3                                                                      OCH.sub.3                                       H   CH.sub.2 CH.sub.2 F                                                                     H     CF.sub.3  OCH.sub.3                                       H   CH.sub.2 CH.sub.2 F                                                                     H     CH.sub.2 F                                                                              OCH.sub.3                                       H   CH.sub.2 CH.sub.2 F                                                                     H     CH.sub.2 Cl                                                                             OCH.sub.3                                       H   CH.sub.2 CH.sub.2 F                                                                     H     CH.sub.2 Br                                                                             OCH.sub.3                                       H   CH.sub.2 CH.sub.2 F                                                                     H     F         OCH.sub.3                                       H   CH.sub.2 CH.sub.2 F                                                                     H     I         OCH.sub.3                                       H   CH.sub.2 CH.sub.2 F                                                                     H     OCH.sub.2 CH.sub.2 F                                                                    OCH.sub.3                                       H   CH.sub.2 CH.sub.2 F                                                                     H     OCH.sub.2 CH.sub.2 CF.sub.3                                                             OCH.sub.3                                       H   CH.sub.2 CH.sub.2 F                                                                     H     OCH.sub.2 CHF.sub.2                                                                     CH.sub.3                                        H   CH.sub.2 CH.sub.2 F                                                                     H     OCH.sub.2 CF.sub.3                                                                      CH.sub.3                                        H   CH.sub.2 CH.sub.2 F                                                                     H     Cl        OC.sub.2 H.sub.5                                H   CH.sub.2 CH.sub.2 F                                                                     H     OC.sub.2 H.sub.5                                                                        NHCH.sub.3                                      H   CH.sub.2 CH.sub.2 F                                                                     H     OCH.sub.3 CH.sub.2 SCH.sub.3                              H   CH.sub.2 CH.sub.2 F                                                                     H     OCF.sub. 2 H                                                                            CH.sub.3                                        H   CH.sub.2 CH.sub.2 F                                                                     H     Cl        OCF.sub.2 H                                     H   CHFCH.sub.3                                                                             H     OCH.sub.3 OC.sub.2 H.sub.5                                H   CHFCH.sub.3                                                                             H     CH.sub.3  OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     CH.sub.3  CH.sub.3                                        H   CHFCH.sub.3                                                                             H     Cl        OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     Br        OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     CH.sub.3  H                                               H   CHFCH.sub.3                                                                             H     OCH.sub.3 H                                               H   CHFCH.sub.3                                                                             H     OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5                       H   CHFCH.sub.3                                                                             H     OCF.sub.2 H                                                                             OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     OCH.sub.3 CH(OCH.sub.3).sub.2                             H   CHFCH.sub.3                                                                             H     CH.sub.3  OC.sub.2 H.sub.5                                H   CHFCH.sub.3                                                                             H     CH.sub.3  CH.sub.2 OCH.sub.3                              H   CHFCH.sub.3                                                                             H     OCH.sub.3 CH.sub.2 OCH.sub.3                              H   CHFCH.sub.3                                                                             H     OCH.sub.3 C.sub.2 H.sub.5                                 H   CHFCH.sub.3                                                                             H     OC.sub.2 H.sub.5                                                                        OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     OCH.sub.2 CF.sub.3                                                                      OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     CF.sub.3  OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     CH.sub.2 F                                                                              OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     CH.sub.2 Cl                                                                             OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     CH.sub.2 Br                                                                             OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     F         OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     I         OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     OCH.sub.2 CH.sub.2 F                                                                    OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     OCH.sub.2 CH.sub.2 CF.sub.3                                                             OCH.sub.3                                       H   CHFCH.sub.3                                                                             H     OCH.sub.2 CHF.sub.2                                                                     CH.sub.3                                        H   CHFCH.sub.3                                                                             H     OCH.sub.2 CF.sub.3                                                                      CH.sub.3                                        H   CHFCH.sub.3                                                                             H     Cl        OC.sub.2 H.sub.5                                H   CHFCH.sub.3                                                                             H     OC.sub.2 H.sub.5                                                                        NHCH.sub.3                                      H   CHFCH.sub.3                                                                             H     OCH.sub.3 CH.sub.2 SCH.sub.3                              H   CHFCH.sub.3                                                                             H     OCF.sub.2 H                                                                             CH.sub.3                                        H   CHFCH.sub.3                                                                             H     Cl        OCF.sub.2 H                                     H   CH.sub.2 Br                                                                             H     OCH.sub.3 OCH.sub.3                                       H   CH.sub.2 Br                                                                             H     CH.sub.3  OCH.sub.3                                       H   CH.sub.2 Br                                                                             H     CH.sub.3  CH.sub.3                                        H   CH.sub.2 Br                                                                             H     Cl        OCH.sub.3                                       H   CH.sub.2 Br                                                                             H     Br        OCH.sub.3                                       H   CH.sub.2 Br                                                                             H     CH.sub.3  H                                               H   CH.sub.2 Br                                                                             H     OCH.sub.3 H                                               H   CH.sub.2 Br                                                                             H     OCH.sub.3 CH.sub.2 OC.sub.2 H.sub.5                       H   CH.sub.2 Br                                                                             H     OCF.sub.2 H                                                                             OCH.sub.3                                       H   CH.sub.2 Br                                                                             H     OCH.sub.3 CH(OCH.sub.3).sub.2                             H   CH.sub.2 Br                                                                             H     CH.sub.3  OC.sub.2 H.sub.5                                H   CH.sub.2 Br                                                                             H     CH.sub.3  CH.sub.2 OCH.sub.3                              H   CH.sub.2 Br                                                                             H     OCH.sub.3 CH.sub.2 OCH.sub.3                              H   CH.sub.2 Br                                                                             H     OCH.sub.3 C.sub.2 H.sub.5                                 H   CH.sub.2 Br                                                                             H     OC.sub.2 H.sub.5                                                                        OCH.sub.3                                       H   CH.sub.2 Br                                                                             H     OCH.sub.2 CF.sub.3                                                                      OCH.sub.3                                       H   CH.sub.2 Br                                                                             H     CF.sub.3  OCH.sub.3                                       H   CH.sub.2 Br                                                                             H     CH.sub.2 F                                                                              OCH.sub.3                                       H   CH.sub.2 Br                                                                             H     CH.sub.2 Cl                                                                             OCH.sub.3                                       H   CH.sub.2 Br                                                                             H     CH.sub.2 Br                                                                             OCH.sub.3                                       H   CH.sub.2 Br                                                                             H     F         OCH.sub.3                                       H   CH.sub.2 Br                                                                             H     I         OCH.sub.3                                       H   CH.sub.2 Br                                                                             H     OCH.sub.2 CH.sub.2 F                                                                    OCH.sub.3                                       H   CH.sub.2 Br                                                                             H     OCH.sub.2 CH.sub.2 CF.sub.3                                                             OCH.sub.3                                       H   CH.sub.2 Br                                                                             H     OCH.sub.2 CHF.sub.2                                                                     CH.sub.3                                        H   CH.sub.2 Br                                                                             H     OCH.sub.2 CF.sub.3                                                                      CH.sub.3                                        H   CH.sub.2 Br                                                                             H     Cl        OC.sub.2 H.sub.5                                H   CH.sub.2 Br                                                                             H     OC.sub.2 H.sub.5                                                                        NHCH.sub.3                                      H   CH.sub.2 Br                                                                             H     OCH.sub.3 CH.sub.2 SCH.sub.3                              H   CH.sub.2 Br                                                                             H     OCF.sub.2 H                                                                             CH.sub. 3                                       H   CH.sub.2 Br                                                                             H     Cl        OCF.sub.2 H                                     ______________________________________                                    

                                      TABLE 4                                     __________________________________________________________________________     ##STR50##                                                                    R.sup.1                                                                              R.sup.2 R.sup.3                                                                           X     Y       mp (°C.)                              __________________________________________________________________________    H      CH.sub.2 F                                                                            H   CH.sub.3                                                                            OCH.sub.3                                                                             137-139                                      H      CH.sub.2 F                                                                            H   OCH.sub.3                                                                           OCH.sub.3                                            H      CH.sub.2 F                                                                            H   OC.sub.2 H.sub.5                                                                    NHCH.sub.3                                           H      CH.sub.2 F                                                                            H   OCH.sub.3                                                                           Cl      138-140                                      H      CH.sub.2 F                                                                            H   OCH.sub.3                                                                           N(CH.sub.3).sub.2                                    H      CH.sub.2 Cl                                                                           H   CH.sub.3                                                                            OCH.sub.3                                                                             95-97                                        H      CH.sub.2 Cl                                                                           H   OCH.sub.3                                                                           OCH.sub.3                                            H      CH.sub.2 Cl                                                                           H   OC.sub.2 H.sub.5                                                                    NHCH.sub.3                                           H      CH.sub.2 Cl                                                                           H   OCH.sub.3                                                                           N(OCH.sub.3)(CH.sub. 3)                              H      CH.sub.2 Cl                                                                           H   OCH.sub.3                                                                           N(CH.sub.3).sub.2                                    H      CH.sub.2 Cl                                                                           H   Cl    OCH.sub.3                                                                             117-120                                      H      CH.sub.2 Br                                                                           H   OCH.sub.3                                                                           OCH.sub.3                                            H      CH.sub.2 Br                                                                           H   OC.sub.2 H.sub.5                                                                    NHCH.sub.3                                           H      CH.sub.2 Br                                                                           H   OCH.sub.3                                                                           N(OCH.sub.3)(CH.sub.3)                               H      CH.sub.2 Br                                                                           H   OCH.sub.3                                                                           N(CH.sub.3).sub.2                                    H      CHF.sub.2                                                                             H   CH.sub.3                                                                            OCH.sub.3                                            H      CHF.sub.2                                                                             H   OCH.sub.3                                                                           OCH.sub.3                                            H      CHF.sub.2                                                                             H   OC.sub.2 H.sub.5                                                                    NHCH.sub.3                                           H      CHF.sub.2                                                                             H   OCH.sub.3                                                                           N(OCH.sub.3)(CH.sub.3)                               H      CHF.sub.2                                                                             H   OCH.sub.3                                                                           N(CH.sub.3).sub.2                                    H      CH.sub.2 F                                                                            CH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                            H      CH.sub.2 Cl                                                                           CH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                            H      CH.sub.2 F                                                                            CH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                            H      CH.sub.2 Br                                                                           CH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                            H      CH.sub.2 Cl                                                                           CH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                            H      CH.sub.2 Br                                                                           CH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                            H      CHF.sub.2                                                                             CH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                            H      CHF.sub.2                                                                             CH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                            H      CH.sub.2 F                                                                            CH.sub.3                                                                          OC.sub.2 H.sub. 5                                                                   NHCH.sub.3                                           H      CH.sub.2 F                                                                            CH.sub.3                                                                          OCH.sub.3                                                                           N(CH.sub.3).sub.2                                    H      CHFCH.sub.3                                                                           H   CH.sub.3                                                                            OCH.sub.3                                                                             96-98                                        H      CHFCH.sub.3                                                                           H   OCH.sub.3                                                                           OCH.sub.3                                            H      CHFCH.sub.3                                                                           H   OC.sub.2 H.sub.5                                                                    NHCH.sub.3                                           H      CHFCH.sub.3                                                                           H   OCH.sub.3                                                                           N(OCH.sub.3)(CH.sub.3)                               H      CHFCH.sub.3                                                                           H   OCH.sub.3                                                                           Cl      112-113                                      H      CHClCH.sub.3                                                                          H   CH.sub.3                                                                            OCH.sub.3                                            H      CHClCH.sub.3                                                                          H   OCH.sub.3                                                                           OCH.sub.3                                            H      CHClCH.sub.3                                                                          H   OC.sub.2 H.sub.5                                                                    NHCH.sub.3                                           H      CHClCH.sub.3                                                                          H   OCH.sub.3                                                                           N(OCH.sub.3)(CH.sub.3)                               H      CHClCH.sub.3                                                                          H   OCH.sub.3                                                                           N(CH.sub.3).sub.2                                    H      CH.sub.2 CH.sub.2 F                                                                   H   CH.sub.3                                                                            OCH.sub.3                                            H      CH.sub.2 CH.sub.2 F                                                                   H   OCH.sub.3                                                                           OCH.sub.3                                            H      CH.sub.2 CH.sub.2 F                                                                   H   OC.sub.2 H.sub.5                                                                    NHCH.sub.3                                           H      CH.sub.2 CH.sub.2 F                                                                   H   OCH.sub.3                                                                           N(OCH.sub.3)(CH.sub.3)                               H      CH.sub.2 CH.sub.2 F                                                                   H   OCH.sub.3                                                                           N(CH.sub.3).sub.2                                    H      CHFCl   H   OCH.sub.3                                                                           OCH.sub.3                                            H      CHFCl   H   CH.sub.3                                                                            OCH.sub.3                                            H      CHFCl   H   CH.sub.3                                                                            CH.sub.3                                             H      CHFCl   H   Cl    OCH.sub.3                                            H      CHFCl   H   OCH.sub.3                                                                           CH.sub.2 OCH.sub.3                                   H      CHFCl   H   CH.sub.3                                                                            OC.sub.2 H.sub.5                                     H      CHFCl   H   CH.sub.2 Cl                                                                         OCH.sub.3                                            H      CHFCl   H   F     OCH.sub.3                                            H      CHFCl   H   OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                  H      CHFCl   H   OCHF.sub.2                                                                          OCH.sub.3                                            H      CHFCH.sub.2 CH.sub.3                                                                  H   CH.sub.3                                                                            OCH.sub.3                                                                             89-91                                        6-F    CH.sub.2 F                                                                            H   CH.sub.3                                                                            OCH.sub.3                                            6-Cl   CH.sub.2 F                                                                            H   OCH.sub.3                                                                           CH.sub.3                                             6-Br   CH.sub.2 F                                                                            H   CH.sub.3                                                                            OCH.sub.3                                            6-CH.sub.2 CN                                                                        CH.sub.2 F                                                                            H   OCH.sub.3                                                                           OCH.sub.3                                            6-OCH.sub.3                                                                          CH.sub.2 F                                                                            H   CH.sub.3                                                                            OCH.sub.3                                            6-SCH.sub.3                                                                          CH.sub.2 F                                                                            H   CH.sub.3                                                                            OCH.sub.3                                            6-OCF.sub.2 H                                                                        CH.sub.2 F                                                                            H   CH.sub.3                                                                            OCH.sub.3                                            6-Cl   CH.sub.2 Cl                                                                           H   CH.sub.3                                                                            OCH.sub.3                                            6-Cl   CH.sub.2 Br                                                                           H   OCH.sub.3                                                                           OCH.sub.3                                            6-Cl   CH.sub.2 F                                                                            H   OC.sub.2 H.sub.5                                                                    NHCH.sub.3                                           6-Cl   CH.sub.2 F                                                                            H   OCH.sub.3                                                                           OCH.sub.3                                            __________________________________________________________________________

                  TABLE 5                                                         ______________________________________                                         ##STR51##                                                                    R.sup.1                                                                             R.sup.2   R.sup.3                                                                              X      Y         mp (°C.)                       ______________________________________                                        H     CH.sub.2 F                                                                              H      CH.sub.3                                                                             OCH.sub.3 148-150                               H     CH.sub.2 F                                                                              H      OCH.sub.3                                                                            OCH.sub.3                                       H     CH.sub.2 F                                                                              H      OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                      H     CH.sub.2 F                                                                              H      OCH.sub.3                                                                            N(OCH.sub.3)(CH.sub.3)                          H     CH.sub.2 F                                                                              H      OCH.sub.3                                                                            N(CH.sub.3).sub.2                               H     CH.sub.2 Cl                                                                             H      CH.sub.3                                                                             OCH.sub.3                                       H     CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                            OCH.sub.3                                       H     CH.sub.2 Cl                                                                             H      OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                      H     CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                            N(OCH.sub.3 )(CH.sub.3)                         H     CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                            N(CH.sub.3).sub.2                               H     CH.sub.2 Br                                                                             H      CH.sub.3                                                                             OCH.sub.3                                       H     CH.sub.2 Br                                                                             H      OCH.sub.3                                                                            OCH.sub.3                                       H     CH.sub.2 Br                                                                             H      OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                      H     CH.sub.2 Br                                                                             H      OCH.sub.3                                                                            N(OCH.sub.3)(CH.sub.3)                          H     CH.sub.2 Br                                                                             H      OCH.sub.3                                                                            N(CH.sub.3).sub.2                               H     CHF.sub.2 H      CH.sub.3                                                                             OCH.sub.3                                       H     CHF.sub.2 H      OCH.sub.3                                                                            OCH.sub.3                                       H     CHF.sub.2 H      OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                      H     CHF.sub.2 H      OCH.sub.3                                                                            N(OCH.sub.3)(CH.sub.3)                          H     CHF.sub.2 H      OCH.sub.3                                                                            N(CH.sub.3).sub.2                               H     CH.sub.2 F                                                                              CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                       H     CH.sub.2 Cl                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                       H     CH.sub.2 F                                                                              CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                       H     CH.sub.2 Br                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                       H     CH.sub.2 Cl                                                                             CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                       H     CH.sub.2 Br                                                                             CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                       H     CHF.sub.2 CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                       H     CHF.sub.2 CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                       H     CH.sub.2 F                                                                              CH.sub.3                                                                             OC.sub.2 H.sub. 5                                                                    NHCH.sub.3                                      H     CH.sub.2 F                                                                              CH.sub.3                                                                             OCH.sub.3                                                                            N(CH.sub.3).sub.2                               H     CHFCH.sub.3                                                                             H      CH.sub.3                                                                             OCH.sub.3                                       H     CHFCH.sub.3                                                                             H      OCH.sub.3                                                                            OCH.sub.3                                       H     CHFCH.sub.3                                                                             H      OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                      H     CHFCH.sub.3                                                                             H      OCH.sub.3                                                                            N(OCH.sub.3)(CH.sub.3)                          H     CHFCH.sub.3                                                                             H      OCH.sub.3                                                                            N(CH.sub.3).sub.2                               H     CHClCH.sub.3                                                                            H      CH.sub.3                                                                             OCH.sub.3                                       H     CHClCH.sub.3                                                                            H      OCH.sub.3                                                                            OCH.sub.3                                       H     CHClCH.sub.3                                                                            H      OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                      H     CHClCH.sub.3                                                                            H      OCH.sub.3                                                                            N(OCH.sub.3)(CH.sub.3)                          H     CHClCH.sub.3                                                                            H      OCH.sub.3                                                                            N(CH.sub.3).sub.2                               H     CH.sub.2 CH.sub.2 F                                                                     H      CH.sub.3                                                                             OCH.sub.3                                       H     CH.sub.2 CH.sub.2 F                                                                     H      OCH.sub.3                                                                            OCH.sub.3                                       H     CH.sub.2 CH.sub.2 F                                                                     H      OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                      H     CH.sub.2 CH.sub.2 F                                                                     H      OCH.sub.3                                                                            N(OCH.sub.3)(CH.sub.3)                          H     CH.sub.2 CH.sub.2 F                                                                     H      OCH.sub.3                                                                            N(CH.sub.3).sub.2                               H     CHFCl     H      OCH.sub.3                                                                            OCH.sub.3                                       H     CHFCl     H      CH.sub.3                                                                             OCH.sub.3                                       H     CHFCl     H      CH.sub.3                                                                             CH.sub.3                                        H     CHFCl     H      Cl     OCH.sub.3                                       H     CHFCl     H      OCH.sub.3                                                                            CH.sub.2 OCH.sub.3                              H     CHFCl     H      CH.sub.3                                                                             OC.sub.2 H.sub.5                                H     CHFCl     H      CH.sub.2 Cl                                                                          OCH.sub.3                                       H     CHFCl     H      F      OCH.sub.3                                       H     CHFCl     H      OCH.sub.3                                                                            CH(OCH.sub.3).sub.2                             H     CHFCl     H      OCHF.sub.2                                                                           OCH.sub.3                                       H     CHFCl     H      C.sub.2 H.sub.5                                                                      OCH.sub.3                                       5-F   CH.sub.2 F                                                                              H      CH.sub.3                                                                             OCH.sub.3                                       ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                         ##STR52##                                                                    R.sup.1                                                                             R.sup.2   R.sup.3                                                                              X      Y         mp (°C.)                       ______________________________________                                        H     CH.sub.2 F                                                                              H      CH.sub.3                                                                             OCH.sub.3                                       H     CH.sub.2 F                                                                              H      OCH.sub.3                                                                            OCH.sub.3                                       H     CH.sub.2 F                                                                              H      OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                      H     CH.sub.2 F                                                                              H      OCH.sub.3                                                                            N(OCH.sub.3)(CH.sub.3)                          H     CH.sub.2 F                                                                              H      OCH.sub.3                                                                            N(CH.sub.3).sub.2                               H     CH.sub.2 Cl                                                                             H      CH.sub.3                                                                             OCH.sub.3                                       H     CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                            OCH.sub.3                                       H     CH.sub.2 Cl                                                                             H      OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                      H     CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                            N(OCH.sub.3)(CH.sub.3)                          H     CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                            N(CH.sub.3).sub.2                               H     CH.sub.2 Br                                                                             H      CH.sub.3                                                                             OCH.sub.3                                       H     CH.sub.2 Br                                                                             H      OCH.sub.3                                                                            OCH.sub.3                                       H     CH.sub.2 Br                                                                             H      OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                      H     CH.sub.2 Br                                                                             H      OCH.sub.3                                                                            N(OCH.sub.2)(CH.sub.3)                          H     CH.sub.2 Br                                                                             H      OCH.sub.3                                                                            N(CH.sub.3).sub.2                               H     CHF.sub.2 H      CH.sub.3                                                                             OCH.sub.3                                       H     CHF.sub.2 H      OCH.sub.3                                                                            OCH.sub.3                                       H     CHF.sub.2 H      OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                      H     CHF.sub.2 H      OCH.sub.3                                                                            N(OCH.sub.3)(CH.sub.3)                          H     CHF.sub.2 H      OCH.sub.3                                                                            N(CH.sub.3).sub.2                               H     CH.sub.2 F                                                                              CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                       H     CH.sub.2 Cl                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                       H     CH.sub.2 F                                                                              CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                       H     CH.sub.2 Br                                                                             CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                                       H     CH.sub.2 Cl                                                                             CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                       H     CH.sub.2 Br                                                                             CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                                       ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                         ##STR53##                                                                    R.sup.1 R.sup.2   R.sup.3 X.sup.1 Y.sup.1                                                                             mp (°C.)                       ______________________________________                                        H       CH.sub.2 F                                                                              H       CH.sub.3                                                                              O                                           H       CH.sub.2 F                                                                              H       OCH.sub.3                                                                             O                                           H       CH.sub.2 F                                                                              H       OC.sub.2 H.sub.5                                                                      O                                           H       CH.sub.2 F                                                                              H       OCF.sub.2 H                                                                           O                                           H       CH.sub.2 F                                                                              H       OCH.sub.3                                                                             CH.sub.2                                    H       CH.sub.2 Cl                                                                             H       CH.sub.3                                                                              O                                           H       CH.sub.2 Cl                                                                             H       OCH.sub.3                                                                             O                                           H       CH.sub.2 Br                                                                             H       CH.sub.3                                                                              O                                           H       CHFCH.sub.3                                                                             H       CH.sub.3                                                                              O                                           H       CHClCH.sub.3                                                                            H       CH.sub.3                                                                              O                                           6-CH.sub.3                                                                            CH.sub.2 F                                                                              H       CH.sub.3                                                                              O                                           6-Cl    CH.sub. 2 F                                                                             H       CH.sub.3                                                                              O                                           4-CH.sub.3                                                                            CH.sub.2 F                                                                              H       CH.sub.3                                                                              O                                           6-CH.sub.2 CN                                                                         CH.sub.2 F                                                                              H       CH.sub.3                                                                              O                                           H       CH.sub.2 F                                                                              CH.sub.3                                                                              CH.sub.3                                                                              O                                           H       CHF.sub.2 H       OCH.sub.3                                                                             O                                           ______________________________________                                    

                  TABLE 8                                                         ______________________________________                                         ##STR54##                                                                    R.sup.1 R.sup.2   R.sup.3 X.sup.1 Y.sup.1                                                                             mp (°C.)                       ______________________________________                                        H       CH.sub.2 F                                                                              H       CH.sub.3                                                                              O                                           H       CH.sub.2 F                                                                              H       OCH.sub.3                                                                             O                                           H       CH.sub.2 F                                                                              H       OC.sub.2 H.sub.5                                                                      O                                           H       CH.sub.2 F                                                                              H       OCF.sub.2 H                                                                           O                                           H       CH.sub.2 F                                                                              H       OCH.sub.3                                                                             CH.sub.2                                    H       CH.sub.2 Cl                                                                             H       CH.sub.3                                                                              O                                           H       CH.sub.2 Cl                                                                             H       OCH.sub.3                                                                             O                                           H       CH.sub.2 Br                                                                             H       CH.sub.3                                                                              O                                           H       CHFCH.sub.3                                                                             H       CH.sub.3                                                                              O                                           H       CHClCH.sub.3                                                                            H       CH.sub.3                                                                              O                                           5-CH.sub.3                                                                            CH.sub.2 F                                                                              H       CH.sub.3                                                                              O                                           5-Cl    CH.sub.2 F                                                                              H       CH.sub.3                                                                              O                                           5-CH.sub.3                                                                            CH.sub.2 F                                                                              H       CH.sub.3                                                                              O                                           5-CH.sub.2 CN                                                                         CH.sub.2 F                                                                              H       CH.sub.3                                                                              O                                           H       CH.sub.2 F                                                                              CH.sub.3                                                                              CH.sub.3                                                                              O                                           H       CHF.sub.2 H       OCH.sub.3                                                                             O                                           ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                         ##STR55##                                                                    R.sup.1 R.sup.2   R.sup.3                                                                              X.sup.1 Y.sup.3                                                                              mp (°C.)                       ______________________________________                                        H       CH.sub.2 F                                                                              H      CH.sub.3                                                                              CH.sub.3                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 F                                                                              H      OC.sub.2 H.sub.5                                                                      CH.sub.3                                     H       CH.sub.2 F                                                                              H      OCF.sub.2 H                                                                           CH.sub.3                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             H                                            H       CH.sub.2 F                                                                              H      CH.sub.3                                                                              H                                            H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             OCH.sub.3                                    H       CHFCl     H      OCH.sub.3                                                                             OCH.sub.3                                    H       CHFCl     H      OCH.sub.3                                                                             CH.sub.3                                     H       CHFCH.sub.3                                                                             H      OCH.sub.3                                                                             OCH.sub.3                                    H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    6-F     CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    6-OCH.sub.3                                                                           CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    6-Cl    CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    6-CH.sub.3                                                                            CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    6-CH.sub.2 CN                                                                         CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 Br                                                                             H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 CH.sub.2 F                                                                     H      OCH.sub.3                                                                             CH.sub.3                                     H       CHClCH.sub.3                                                                            H      OCH.sub.3                                                                             CH.sub.3                                     H       CHF.sub.2 CH.sub.3                                                                             OCH.sub.3                                                                             CH.sub.3                                     6-Cl    CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                     ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                         ##STR56##                                                                    R.sup.1 R.sup.2    R.sup.3                                                                              X.sup.1 Y.sup.1                                                                             mp (°C.)                       ______________________________________                                        H       CH.sub.2 F H      CH.sub.3                                                                              O                                           H       CH.sub.2 F H      OCH.sub.3                                                                             O                                           H       CH.sub.2 F H      OC.sub.2 H.sub.5                                                                      O                                           H       CH.sub.2 F H      OCF.sub.2 H                                                                           O                                           H       CH.sub.2 F H      OCH.sub.3                                                                             CH.sub.2                                    H       CH.sub.2 Cl                                                                              H      CH.sub.3                                                                              O                                           H       CH.sub.2 Cl                                                                              H      OCH.sub.3                                                                             O                                           H       CH.sub.2 Br                                                                              H      CH.sub.3                                                                              O                                           H       CHFCH.sub.3                                                                              H      CH.sub.3                                                                              O                                           H       CHClCH.sub.3                                                                             H      CH.sub.3                                                                              O                                           2-CH.sub.3                                                                            CH.sub.2 F H      CH.sub.3                                                                              O                                           2-Cl    CH.sub. 2 F                                                                              H      CH.sub.3                                                                              O                                           2-CH.sub.3                                                                            CH.sub.2 F H      CH.sub.3                                                                              O                                           2-CH.sub.2 CN                                                                         CH.sub.2 F H      CH.sub.3                                                                              O                                           H       CH.sub.2 F H      CH.sub.3                                                                              O                                           H       CHF.sub.2  H      OCH.sub.3                                                                             O                                           ______________________________________                                    

                  TABLE 11                                                        ______________________________________                                         ##STR57##                                                                    R.sup.1 R.sup.2   R.sup.3                                                                              X.sup.1 Y.sup.3                                                                              mp (°C.)                       ______________________________________                                        H       CH.sub.2 F                                                                              H      CH.sub.3                                                                              CH.sub.3                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 F                                                                              H      OC.sub.2 H.sub.5                                                                      CH.sub.3                                     H       CH.sub.2 F                                                                              H      OCF.sub.2 H                                                                           CH.sub.3                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             H                                            H       CH.sub.2 F                                                                              H      CH.sub.3                                                                              H                                            H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             OCH.sub.3                                    H       CHFCl     H      OCH.sub.3                                                                             OCH.sub.3                                    H       CHFCl     H      OCH.sub.3                                                                             CH.sub.3                                     H       CHFCH.sub.3                                                                             H      OCH.sub.3                                                                             OCH.sub.3                                    H       CH.sub.2 F                                                                              H      OCH.sub. 3                                                                            OCH.sub.3                                    5-F     CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    5-OCH.sub.3                                                                           CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    5-Cl    CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    5-CH.sub.3                                                                            CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    5-CH.sub.2 CN                                                                         CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 Br                                                                             H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 CH.sub.2 F                                                                     H      OCH.sub.3                                                                             CH.sub.3                                     H       CHClCH.sub.3                                                                            H      OCH.sub.3                                                                             CH.sub.3                                     H       CHF.sub.2 H      OCH.sub.3                                                                             CH.sub.3                                     4-Cl    CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                     ______________________________________                                    

                  TABLE 12                                                        ______________________________________                                         ##STR58##                                                                    R.sup.1 R.sup.2    R.sup.3   X.sup.1                                                                              mp (°C.)                           ______________________________________                                        H       CH.sub.2 F H         CH.sub.3                                         H       CH.sub.2 F H         OCH.sub.3                                        H       CH.sub.2 F H         OC.sub.2 H.sub.5                                 H       CH.sub.2 F H         OCF.sub.2 H                                      H       CH.sub.2 Cl                                                                              H         CH.sub.3                                         H       CH.sub.2 Cl                                                                              H         OCH.sub.3                                        H       CH.sub.2 Br                                                                              H         CH.sub.3                                         H       CHF.sub.2  H         CH.sub.3                                         H       CHF.sub.2  H         OCH.sub.3                                        H       CHFCH.sub.3                                                                              H         CH.sub.3                                         H       CHFCH.sub.3                                                                              H         OCH.sub.3                                        H       CHFCl      H         OCH.sub.3                                        H       CHFCl      H         CH.sub.3                                         2-Cl    CHFCl      H         CH.sub.3                                         2-Cl    CHFCl      H         OCH.sub.3                                        2-Cl    CH.sub. 2 F                                                                              H         CH.sub.3                                         2-Cl    CH.sub.2 F H         OCH.sub.3                                        2-CH.sub.2                                                                            CH.sub.2 F H         CH.sub.3                                         2-OCH.sub.3                                                                           CH.sub.2 F H         CH.sub.3                                         H       CH.sub.2 F CH.sub.3  CH.sub.3                                         H       CH.sub.2 F CH.sub.3  OCH.sub.3                                        H       CHClCH.sub.3                                                                             H         OCH.sub.3                                        H       CH.sub.2 CH.sub.2 F                                                                      H         OCH.sub.3                                        ______________________________________                                    

                  TABLE 13                                                        ______________________________________                                         ##STR59##                                                                    R.sup.1 R.sup.2   R.sup.3                                                                              X.sup.1 Y.sup.3                                                                              mp (°C.)                       ______________________________________                                        H       CH.sub.2 F                                                                              H      CH.sub.3                                                                              CH.sub.3                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 F                                                                              H      OC.sub.2 H.sub.5                                                                      CH.sub.3                                     H       CH.sub.2 F                                                                              H      OCF.sub.2 H                                                                           CH.sub.3                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             H                                            H       CH.sub.2 F                                                                              H      CH.sub.3                                                                              H                                            H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             OCH.sub.3                                    H       CHFCl     H      OCH.sub.3                                                                             OCH.sub.3                                    H       CHFCl     H      OCH.sub.3                                                                             CH.sub.3                                     H       CHFCH.sub.3                                                                             H      OCH.sub.3                                                                             OCH.sub.3                                    H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    2-F     CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    2-OCH.sub.3                                                                           CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    2-Cl    CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    2-CH.sub.3                                                                            CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    2-CH.sub.3                                                                            CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 Br                                                                             H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 CH.sub.2 F                                                                     H      OCH.sub.3                                                                             CH.sub.3                                     H       CHClCH.sub.3                                                                            H      OCH.sub.3                                                                             CH.sub.3                                     H       CHF.sub.2 H      OCH.sub.3                                                                             CH.sub.3                                     5-Cl    CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                     ______________________________________                                    

                  TABLE 14                                                        ______________________________________                                         ##STR60##                                                                    R.sup.1 R.sup.2   R.sup.3                                                                              X.sup.1 Y.sup.3                                                                              mp (°C.)                       ______________________________________                                        H       CH.sub.2 F                                                                              H      CH.sub.3                                                                              CH.sub.3                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 F                                                                              H      OC.sub.2 H.sub.5                                                                      CH.sub.3                                     H       CH.sub.2 F                                                                              H      OCF.sub.2 H                                                                           CH.sub.3                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             H                                            H       CH.sub.2 F                                                                              H      CH.sub.3                                                                              H                                            H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             OCH.sub.3                                    H       CHFCl     H      OCH.sub.3                                                                             OCH.sub.3                                    H       CHFCl     H      OCH.sub.3                                                                             CH.sub.3                                     H       CHFCH.sub.3                                                                             H      OCH.sub.3                                                                             OCH.sub.3                                    H       CH.sub. 2 F                                                                             H      OCH.sub.3                                                                             OCH.sub.3                                    6-F     CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    6-OCH.sub.3                                                                           CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    6-Cl    CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    4-CH.sub.3                                                                            CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    6-CH.sub.2 CN                                                                         CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 Br                                                                             H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 CH.sub.2 F                                                                     H      OCH.sub.3                                                                             CH.sub.3                                     H       CHClCH.sub.3                                                                            H      OCH.sub.3                                                                             CH.sub.3                                     H       CHF.sub.2 H      OCH.sub.3                                                                             CH.sub.3                                     6-Cl    CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                     ______________________________________                                    

                  TABLE 15                                                        ______________________________________                                         ##STR61##                                                                    R.sup.1 R.sup.2   R.sup.3                                                                              X.sup.1 Y.sup.3                                                                              mp (°C.)                       ______________________________________                                        H       CH.sub.2 F                                                                              H      CH.sub.3                                                                              CH.sub.3                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 F                                                                              H      OC.sub.2 H.sub.5                                                                      CH.sub.3                                     H       CH.sub.2 F                                                                              H      OCF.sub.2 H                                                                           CH.sub.3                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             H                                            H       CH.sub.2 F                                                                              H      CH.sub.3                                                                              H                                            H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             OCH.sub.3                                    H       CHFCl     H      OCH.sub.3                                                                             OCH.sub.3                                    H       CHFCl     H      OCH.sub.3                                                                             CH.sub.3                                     H       CHFCH.sub.3                                                                             H      OCH.sub.3                                                                             OCH.sub.3                                    H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    5-F     CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    5-OCH.sub.3                                                                           CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    5-Cl    CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    5-CH.sub.3                                                                            CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                    5-CH.sub.2 CN                                                                         CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 Br                                                                             H      OCH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 CH.sub.2 F                                                                     H      OCH.sub.3                                                                             CH.sub.3                                     H       CHClCH.sub.3                                                                            H      OCH.sub.3                                                                             CH.sub.3                                     H       CHF.sub.2 H      OCH.sub.3                                                                             CH.sub.3                                     5-Cl    CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                     ______________________________________                                    

                  TABLE 16                                                        ______________________________________                                         ##STR62##                                                                    R.sup.1 R.sup.2   R.sup.3 X.sup.2                                                                              Y.sup.2                                                                              mp (°C.)                       ______________________________________                                        H       CH.sub.2 F                                                                              H       CH.sub.3                                                                             OCH.sub.3                                    H       CH.sub.2 F                                                                              H       CH.sub.3                                                                             OC.sub.2 H.sub.5                             H       CH.sub.2 F                                                                              H       CH.sub.3                                                                             SCH.sub.3                                    H       CH.sub.2 F                                                                              H       CH.sub.3                                                                             SC.sub.2 H.sub.5                             H       CH.sub.2 F                                                                              H       CH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 F                                                                              H       CH.sub.3                                                                             C.sub.2 H.sub.5                              H       CH.sub.2 F                                                                              H       C.sub.2 H.sub.5                                                                      OCH.sub.3                                    H       CH.sub.2 F                                                                              H       CH.sub.2 CF.sub.3                                                                    OCH.sub.3                                    H       CH.sub.2 Cl                                                                             H       CH.sub.3                                                                             OCH.sub.3                                    H       CHFCl     H       CH.sub. 3                                                                            OCH.sub.3                                    H       CHF.sub.2 H       CH.sub.3                                                                             OCH.sub.3                                    5-CH.sub.3                                                                            CH.sub.2 F                                                                              H       CH.sub.3                                                                             OCH.sub.3                                    5-F     CH.sub.2 F                                                                              H       CH.sub.3                                                                             OCH.sub.3                                    5-Cl    CH.sub.2 F                                                                              H       CH.sub.3                                                                             OCH.sub.3                                    5-OCH.sub.3                                                                           CH.sub.2 F                                                                              H       CH.sub.3                                                                             OCH.sub.3                                    5-Cl    CH.sub.2 F                                                                              H       CH.sub.3                                                                             CH.sub.3                                     5-CH.sub.2 CN                                                                         CH.sub.2 F                                                                              H       CH.sub.3                                                                             OCH.sub.3                                    H       CH.sub.2 Br                                                                             H       CH.sub.3                                                                             OCH.sub.3                                    H       CH.sub.2 CH.sub.2 F                                                                     H       CH.sub.3                                                                             OCH.sub.3                                    H       CHFCl     H       CH.sub.3                                                                             CH.sub.3                                     H       CHFCH.sub.3                                                                             H       CH.sub.3                                                                             OCH.sub.3                                    H       CHClCH.sub.3                                                                            H       CH.sub.3                                                                             OCH.sub.3                                    ______________________________________                                    

                  TABLE 17                                                        ______________________________________                                         ##STR63##                                                                    R.sup.1 R.sup.2   R.sup.3 X.sup.2                                                                              Y.sup.2                                                                              mp (°C.)                       ______________________________________                                        H       CH.sub.2 F                                                                              H       CH.sub.3                                                                             OCH.sub.3                                    H       CH.sub.2 F                                                                              H       CH.sub.3                                                                             OC.sub.2 H.sub.5                             H       CH.sub.2 F                                                                              H       CH.sub.3                                                                             SCH.sub.3                                    H       CH.sub.2 F                                                                              H       CH.sub.3                                                                             SC.sub.2 H.sub.5                             H       CH.sub.2 F                                                                              H       CH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 F                                                                              H       CH.sub.3                                                                             C.sub.2 H.sub.5                              H       CH.sub.2 F                                                                              H       C.sub.2 H.sub.5                                                                      OCH.sub.3                                    H       CH.sub.2 F                                                                              H       CH.sub.2 CF.sub.3                                                                    OCH.sub.3                                    H       CH.sub.2 Cl                                                                             H       CH.sub.3                                                                             OCH.sub.3                                    H       CHFCl     H       CH.sub.3                                                                             OCH.sub.3                                    H       CHF.sub.2 H       CH.sub.3                                                                             OCH.sub.3                                    6-CH.sub.3                                                                            CH.sub.2 F                                                                              H       CH.sub.3                                                                             OCH.sub.3                                    6-F     CH.sub.2 F                                                                              H       CH.sub.3                                                                             OCH.sub.3                                    6-Cl    CH.sub.2 F                                                                              H       CH.sub.3                                                                             OCH.sub.3                                    6-OCH.sub.3                                                                           CH.sub.2 F                                                                              H       CH.sub.3                                                                             OCH.sub.3                                    6-Cl    CH.sub.2 F                                                                              H       CH.sub.3                                                                             CH.sub.3                                     6-CH.sub.2 CN                                                                         CH.sub.2 F                                                                              H       CH.sub.3                                                                             OCH.sub.3                                    H       CH.sub.2 Br                                                                             H       CH.sub.3                                                                             OCH.sub.3                                    H       CH.sub.2 CH.sub.2 F                                                                     H       CH.sub.3                                                                             OCH.sub.3                                    H       CHFCl     H       CH.sub.3                                                                             CH.sub.3                                     H       CHFCH.sub.3                                                                             H       CH.sub.3                                                                             OCH.sub.3                                    H       CHClCH.sub.3                                                                            H       CH.sub.3                                                                             OCH.sub.3                                    ______________________________________                                    

                  TABLE 18                                                        ______________________________________                                         ##STR64##                                                                    R.sup.1 R.sup.2   R.sup.3 X.sup.2                                                                              Y.sup.2                                                                              mp (°C.)                       ______________________________________                                        H       CH.sub.2 F                                                                              H       CH.sub.3                                                                             OCH.sub.3                                    H       CH.sub.2 F                                                                              H       CH.sub.3                                                                             OC.sub.2 H.sub.5                             H       CH.sub.2 F                                                                              H       CH.sub.3                                                                             SCH.sub.3                                    H       CH.sub.2 F                                                                              H       CH.sub.3                                                                             SC.sub.2 H.sub.5                             H       CH.sub.2 F                                                                              H       CH.sub.3                                                                             CH.sub.3                                     H       CH.sub.2 F                                                                              H       CH.sub.3                                                                             C.sub.2 H.sub.5                              H       CH.sub.2 F                                                                              H       C.sub.2 H.sub.5                                                                      OCH.sub.3                                    H       CH.sub.2 F                                                                              H       CH.sub.2 CF.sub.3                                                                    OCH.sub.3                                    H       CH.sub.2 Cl                                                                             H       CH.sub.3                                                                             OCH.sub.3                                    H       CHFCl     H       CH.sub.3                                                                             OCH.sub. 3                                   H       CHF.sub.2 H       CH.sub.3                                                                             OCH.sub.3                                    2-CH.sub.3                                                                            CH.sub.2 F                                                                              H       CH.sub.3                                                                             OCH.sub.3                                    2-F     CH.sub.2 F                                                                              H       CH.sub.3                                                                             OCH.sub.3                                    2-Cl    CH.sub.2 F                                                                              H       CH.sub.3                                                                             OCH.sub.3                                    2-OCH.sub.3                                                                           CH.sub.2 F                                                                              H       CH.sub.3                                                                             OCH.sub.3                                    2-Cl    CH.sub.2 F                                                                              H       CH.sub.3                                                                             CH.sub.3                                     2-CH.sub.2 CN                                                                         CH.sub.2 F                                                                              H       CH.sub.3                                                                             OCH.sub.3                                    H       CH.sub.2 Br                                                                             H       CH.sub.3                                                                             OCH.sub.3                                    H       CH.sub.2 CH.sub.2 F                                                                     H       CH.sub.3                                                                             OCH.sub.3                                    H       CHFCl     H       CH.sub.3                                                                             CH.sub.3                                     H       CHFCH.sub.3                                                                             H       CH.sub.3                                                                             OCH.sub.3                                    H       CHClCH.sub.3                                                                            H       CH.sub.3                                                                             OCH.sub.3                                    ______________________________________                                    

                  TABLE 19                                                        ______________________________________                                         ##STR65##                                                                    R.sup.1  R.sup.2    R.sup.3  X.sup.3                                                                             mp (°C.)                            ______________________________________                                        H        CH.sub.2 F H        CH.sub.3                                         H        CH.sub.2 F H        OCH.sub.3                                        H        CH.sub.2 Cl                                                                              H        CH.sub.3                                         H        CH.sub.2 Cl                                                                              H        OCH.sub.3                                        H        CHF.sub.2  H        OCH.sub.3                                        H        CHF.sub.2  H        CH.sub.3                                         H        CHFCl      H        CH.sub.3                                         H        CHFCl      H        OCH.sub.3                                        H        CHFCH.sub.3                                                                              H        CH.sub.3                                         H        CHFCH.sub.3                                                                              H        OCH.sub.3                                        H        CHClCH.sub.3                                                                             H        OCH.sub.3                                        5-F      CH.sub.2 F H        OCH.sub.3                                        5-Cl     CH.sub.2 F H        OCH.sub.3                                        5-CH.sub.3                                                                             CH.sub.2 F H        CH.sub. 3                                        5-OCH.sub.3                                                                            CH.sub.2 F H        CH.sub.3                                         5-CH.sub.2 CN                                                                          CH.sub.2 F H        CH.sub.3                                         5-Cl     CH.sub.2 F H        OCH.sub.3                                        H        CH.sub.2 CH.sub.2 F                                                                      H        OCH.sub.3                                        H        CH.sub.2 F CH.sub.3 OCH.sub.3                                        H        CH.sub.2 CH.sub.2 F                                                                      H        CH.sub.3                                         ______________________________________                                    

                  TABLE 20                                                        ______________________________________                                         ##STR66##                                                                    R.sup.1  R.sup.2    R.sup.3  X.sup.3                                                                             mp (°C.)                            ______________________________________                                        H        CH.sub.2 F H        CH.sub.3                                         H        CH.sub.2 F H        OCH.sub.3                                        H        CH.sub.2 Cl                                                                              H        CH.sub.3                                         H        CH.sub.2 Cl                                                                              H        OCH.sub.3                                        H        CHF.sub.2  H        OCH.sub.3                                        H        CHF.sub.2  H        CH.sub.3                                         H        CHFCl      H        CH.sub.3                                         H        CHFCl      H        OCH.sub.3                                        H        CHFCH.sub.3                                                                              H        CH.sub.3                                         H        CHFCH.sub.3                                                                              H        OCH.sub.3                                        H        CHClCH.sub.3                                                                             H        OCH.sub.3                                        6-F      CH.sub.2 F H        OCH.sub.3                                        6-Cl     CH.sub.2 F H        OCH.sub.3                                        6-CH.sub.3                                                                             CH.sub.2 F H        CH.sub.3                                         6-OCH.sub.3                                                                            CH.sub.2 F H        CH.sub.3                                         6-CH.sub.2 CN                                                                          CH.sub.2 F H        CH.sub.3                                         6-Cl     CH.sub.2 F H        OCH.sub.3                                        H        CH.sub.2 CH.sub.2 F                                                                      H        OCH.sub.3                                        H        CH.sub.2 F CH.sub.3 OCH.sub.3                                        H        CH.sub.2 CH.sub.2 F                                                                      H        CH.sub.3                                         ______________________________________                                    

                  TABLE 21                                                        ______________________________________                                         ##STR67##                                                                    R.sup.1  R.sup.2    R.sup.3  X.sup.3                                                                             mp (°C.)                            ______________________________________                                        H        CH.sub.2 F H        CH.sub.3                                         H        CH.sub.2 F H        OCH.sub.3                                        H        CH.sub.2 Cl                                                                              H        CH.sub.3                                         H        CH.sub.2 Cl                                                                              H        OCH.sub.3                                        H        CHF.sub.2  H        OCH.sub.3                                        H        CHF.sub.2  H        CH.sub.3                                         H        CHFCl      H        CH.sub.3                                         H        CHFCl      H        OCH.sub.3                                        H        CHFCH.sub.3                                                                              H        CH.sub.3                                         H        CHFCH.sub.3                                                                              H        OCH.sub.3                                        H        CHClCH.sub.3                                                                             H        OCH.sub.3                                        2-F      CH.sub.2 F H        OCH.sub.3                                        2-Cl     CH.sub.2 F H        OCH.sub.3                                        2-CH.sub.3                                                                             CH.sub.2 F H        CH.sub.3                                         2-OCH.sub.3                                                                            CH.sub.2 F H        CH.sub.3                                         2-CH.sub.2 CN                                                                          CH.sub.2 F H        CH.sub.3                                         2-Cl     CH.sub.2 F H        OCH.sub.3                                        H        CH.sub.2 CH.sub.2 F                                                                      H        OCH.sub.3                                        H        CH.sub.2 F CH.sub.3 OCH.sub.3                                        H        CH.sub.2 CH.sub.2 F                                                                      H        CH.sub.3                                         ______________________________________                                    

                  TABLE 22                                                        ______________________________________                                         ##STR68##                                                                                                                mp                                R.sup.1 R.sup.2   R.sup.3                                                                              X.sup.4 Y.sup.4                                                                             Z.sup.1                                                                            (°C.)                      ______________________________________                                        H       CH.sub.2 F                                                                              H      CH.sub.3                                                                              CH.sub.3                                                                            CH                                     H       CH.sub.2 F                                                                              H      CH.sub.3                                                                              CH.sub.3                                                                            N                                      H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            N                                      H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                                                           N                                      H       CH.sub.2 F                                                                              H      Cl      CH.sub.3                                                                            CH                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             Cl    CH                                     H       CH.sub.2 F                                                                              H      OC.sub.2 H.sub.5                                                                      CH.sub.3                                                                            CH                                     H       CH.sub.2 F                                                                              H      CH.sub.2 OCH.sub.3                                                                    CH.sub.3                                                                            N                                      H       CH.sub.2 F                                                                              H      CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                           CH                                     H       CH.sub.2 F                                                                              H      OC.sub.2 H.sub.5                                                                      OC.sub.2 H.sub.5                                                                    N                                      H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                     H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             CH.sub.3                                                                            N                                      H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             OCH.sub.3                                                                           N                                      H       CHF.sub.2 H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CHFCl     H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CHFCH.sub.3                                                                             H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CHClCH.sub.3                                                                            H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     5-F     CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     5-CH.sub.3                                                                            CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     5-OCH.sub.3                                                                           CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     5-Cl    CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     5-CH.sub.2 CN                                                                         CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CH.sub.2 F                                                                              CH.sub.3                                                                             OCH.sub. 3                                                                            CH.sub.3                                                                            CH                                     H       CH.sub.2 CH.sub.2 F                                                                     H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CH.sub.2 CH.sub.2 Cl                                                                    H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CHFCl     H      OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                     ______________________________________                                    

                  TABLE 23                                                        ______________________________________                                         ##STR69##                                                                                                                mp                                R.sup.1 R.sup.2   R.sup.3                                                                              X.sup.4 Y.sup.4                                                                             Z.sup.1                                                                            (°C.)                      ______________________________________                                        H       CH.sub.2 F                                                                              H      CH.sub.3                                                                              CH.sub.3                                                                            CH                                     H       CH.sub.2 F                                                                              H      CH.sub.3                                                                              CH.sub.3                                                                            N                                      H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            N                                      H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                                                           N                                      H       CH.sub.2 F                                                                              H      Cl      CH.sub.3                                                                            CH                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             Cl    CH                                     H       CH.sub.2 F                                                                              H      OC.sub.2 H.sub.5                                                                      CH.sub.3                                                                            CH                                     H       CH.sub.2 F                                                                              H      CH.sub.2 OCH.sub.3                                                                    CH.sub.3                                                                            N                                      H       CH.sub.2 F                                                                              H      CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                           CH                                     H       CH.sub.2 F                                                                              H      OC.sub.2 H.sub.5                                                                      OC.sub.2 H.sub.5                                                                    N                                      H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                     H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             CH.sub.3                                                                            N                                      H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             OCH.sub.3                                                                           N                                      H       CHF.sub.2 H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CHFCl     H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CHFCH.sub.3                                                                             H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CHClCH.sub.3                                                                            H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     6-F     CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     6-CH.sub.3                                                                            CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     6-OCH.sub.3                                                                           CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     6-Cl    CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     6-CH.sub.2 CN                                                                         CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CH.sub.2 F                                                                              CH.sub.3                                                                             OCH.sub.3                                                                             CH.sub. 3                                                                           CH                                     H       CH.sub.2 CH.sub.2 F                                                                     H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CH.sub.2 CH.sub.2 Cl                                                                    H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CHFCl     H      OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                     ______________________________________                                    

                  TABLE 24                                                        ______________________________________                                         ##STR70##                                                                                                                mp                                R.sup.1 R.sup.2   R.sup.3                                                                              X.sup.4 Y.sup.4                                                                             Z.sup.1                                                                            (°C.)                      ______________________________________                                        H       CH.sub.2 F                                                                              H      CH.sub.3                                                                              CH.sub.3                                                                            CH                                     H       CH.sub.2 F                                                                              H      CH.sub.3                                                                              CH.sub.3                                                                            N                                      H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            N                                      H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             OCH.sub.3                                                                           N                                      H       CH.sub.2 F                                                                              H      Cl      CH.sub. 3                                                                           CH                                     H       CH.sub.2 F                                                                              H      OCH.sub.3                                                                             Cl    CH                                     H       CH.sub.2 F                                                                              H      OC.sub.2 H.sub.5                                                                      CH.sub.3                                                                            CH                                     H       CH.sub.2 F                                                                              H      CH.sub.2 OCH.sub.3                                                                    CH.sub.3                                                                            N                                      H       CH.sub.2 F                                                                              H      CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                           CH                                     H       CH.sub.2 F                                                                              H      OC.sub.2 H.sub.5                                                                      OC.sub.2 H.sub.5                                                                    N                                      H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                     H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             CH.sub.3                                                                            N                                      H       CH.sub.2 Cl                                                                             H      OCH.sub.3                                                                             OCH.sub.3                                                                           N                                      H       CHF.sub.2 H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CHFCl     H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CHFCH.sub.3                                                                             H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CHClCH.sub.3                                                                            H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     2-F     CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     2-CH.sub.3                                                                            CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     2-OCH.sub.3                                                                           CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     2-Cl    CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     2-CH.sub.2 CH                                                                         CH.sub.2 F                                                                              H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CH.sub.2 F                                                                              CH.sub.3                                                                             OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CH.sub.2 CH.sub.2 F                                                                     H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CH.sub.2 CH.sub.2 Cl                                                                    H      OCH.sub.3                                                                             CH.sub.3                                                                            CH                                     H       CHFCl     H      OCH.sub.3                                                                             OCH.sub.3                                                                           CH                                     ______________________________________                                    

                  TABLE 25                                                        ______________________________________                                         ##STR71##                                                                                                                  mp                              R.sup.1                                                                              R.sup.2   R.sup.3                                                                              W    X     Y     Z.sup.1                                                                            (°C.)                    ______________________________________                                        H      CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CH.sub.2 F                                                                              H      S    CH.sub.3                                                                            OCH.sub.3                                                                           N                                    H      CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    H      CH.sub.2 Cl                                                                             H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CH.sub.2 Br                                                                             H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CHF.sub.2 H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CHFCl     H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CHFCH.sub. 3                                                                            H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CHClCH.sub.3                                                                            H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   5-OCH.sub.3                                                                          CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   5-Cl   CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CH.sub.2 F                                                                              CH.sub.3                                                                             S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           CH.sub.3                                                                            CH                                   ______________________________________                                    

                  TABLE 26                                                        ______________________________________                                         ##STR72##                                                                                                                  mp                              R.sup.1                                                                              R.sup.2   R.sup.3                                                                              W    X     Y     Z.sup.1                                                                            (°C.)                    ______________________________________                                        H      CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CH.sub.2 F                                                                              H      S    CH.sub.3                                                                            OCH.sub.3                                                                           N                                    H      CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    H      CH.sub.2 Cl                                                                             H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CH.sub.2 Br                                                                             H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CHF.sub.2 H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CHFCl     H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CHFCH.sub.3                                                                             H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CHClCH.sub.3                                                                            H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   6-OCH.sub.3                                                                          CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   6-Cl   CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CH.sub.2 F                                                                              CH.sub.3                                                                             S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           CH.sub.3                                                                            CH                                   ______________________________________                                    

                  TABLE 27                                                        ______________________________________                                         ##STR73##                                                                                                                  mp                              R.sup.1                                                                              R.sup.2   R.sup.3                                                                              W    X     Y     Z.sup.1                                                                            (°C.)                    ______________________________________                                        H      CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CH.sub.2 F                                                                              H      S    CH.sub.3                                                                            OCH.sub.3                                                                           N                                    H      CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    H      CH.sub.2 Cl                                                                             H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CH.sub.2 Br                                                                             H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CHF.sub.2 H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CHFCl     H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CHFCH.sub.3                                                                             H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CHClCH.sub.3                                                                            H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   2-OCH.sub.3                                                                          CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   2-Cl   CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CH.sub.2 F                                                                              CH.sub.3                                                                             S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           CH.sub.3                                                                            CH                                   ______________________________________                                    

                  TABLE 28                                                        ______________________________________                                         ##STR74##                                                                                                                  mp                              R.sup.1                                                                              R.sup.2   R.sup.3                                                                              W    X     Y     Z.sup.1                                                                            (°C.)                    ______________________________________                                        H      CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CH.sub.2 F                                                                              H      S    CH.sub.3                                                                            OCH.sub.3                                                                           N                                    H      CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           N                                    H      CH.sub.2 Cl                                                                             H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CH.sub.2 Br                                                                             H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CHF.sub.2 H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CHFCl     H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CHFCH.sub. 3                                                                            H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CHClCH.sub.3                                                                            H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   5-OCH.sub.3                                                                          CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   5-Cl   CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CH.sub.2 F                                                                              CH.sub.3                                                                             S    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                   H      CH.sub.2 F                                                                              H      S    OCH.sub.3                                                                           CH.sub.3                                                                            CH                                   ______________________________________                                    

Test results indicate that the compounds of the present invention arehighly active pre-emergent or post-emergent herbicides or plant growthregulants. Many of them have utility for broad-spectrum pre- and/orpost-emergency weed control in areas where complete control of allvegetation is desired, such as around fuel storage tanks, ammunitiondepots, industrial storage areas, parking lots, drive-in theaters,around billboards, highway and railroad structures. Some of thecompounds have utility for selective weed control in crops such as wheatand barley. Alternatively, the subject compounds are useful to modifyplant growth.

The rates of application for the compounds of the present invention aredetermined by a number of factors, including their use as plant growthmodifiers or as herbicides, the crop species involved, the types ofweeds to be controlled, weather and climate, formulations selected, modeof application, amount of foliage present, etc.

In general terms, the subject compounds should be applied at levels ofaround 0.05 to 10 kg/ha, the lower rates being suggested for use onlighter soils and/or those having a low organic matter content, forplant growth modifications or for situations where only short-termpersistence is required.

Formulations

Useful formulations of the compounds of formula(I) can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly.

Sprayable formulations can be extented in suitable media and used atspray volumes of from a few liters to several hundred liters perhectare. High strength compositions are primarily used as intermediatesfor further formulation. The formulations, broadly, contain about 0.1%to 99% by weight of active ingredient(s) and at least one of (1) about0.1% to 20% surfactant(s) and (2) about 1% to 99.9% solid or liquidinert diluent(s). More specially, they will contain these ingredients inthe following approximate proportions:

    ______________________________________                                                      Weight Percent*                                                                 Active              Surfact-                                  Formulations    Ingredient                                                                              Diluent(s)                                                                              ant(s)                                    ______________________________________                                        Wettable Powders                                                                              20-90      0-74     1-10                                      Oil Suspensions, Emulsions,                                                                    3-50     40-95     0-15                                      Solutions (including                                                          Emulsifiable concentrates)                                                    Aqueous Suspension                                                                            10-50     40-84     1-20                                      Dusts            1-25     70-99     0-5                                       Granules and Pellets                                                                          0.1-95      5-99.9  0-15                                      High Strength Compositions                                                                    90-99      0-10     0-2                                       ______________________________________                                         *Active ingredient plus at least one of a surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactants to activate ingredient aresometimes desirable, and are achieved by incorporation into theformation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N.J., but other solids, either mined or monufactured, may beused. The more absorptive diluents are preferred for wettable powdersand the denser ones for dusts.

Typical liquid diluents and solvents are described in Marsden, "SolventGuide", 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% ispreferred for suspension concentrates; Solution concentrates arepreferably stable against phase separation at 0° C. "McCutcheon'sDetergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood,N.J., as well as Sisely and Wood, "Encyclopedia of Surface ActiveAgents", Chemical Publishing Co., Inc., New York, 1964, list surfactantsand recommended uses.

All formulations can contain minor amounts of additives to reducefoaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques.

See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967,pp, 147ff. and "Perry's chemical Engineer's Handbook", 5th Ed.,McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41; R. W. Luckenbaugh,U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7,line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140,162-164, 166, 167 and 169-182; H. Gysin and E. Knusli, U.S. Pat. No.2,891,855, Jun. 23, 1959, Col. 3, line 66 through Col. 5, line 17 andExamples 1-4; G. C. Klingman, "Weed Control as a Science", John Wileyand S. A. Evans, "Weed control Handbook", 5th Ed., Blackwell ScientificPublications, Oxford, 1968, pp. 101-103.

The compounds of the present invention can be used independently and maybe used in combination with any other commercial herbicide. A summary ofthe possible combination herbicides is given below.

    ______________________________________                                        Common Name                                                                   ______________________________________                                        acetochlor  acifluorfen   AC 252,214                                          AC 263,499  acrolein      alachlor                                            ametryn     amitrole      AMS                                                 asulam      assure        atrazine                                            BAS-514     barban        benefin                                             bensulfuron methyl                                                                        bensulide     bentazon                                            benzofluor  benzoylprop   bifenox                                             bromacil    bromoxynil    butachlor                                           buthidazole butralin      butylate                                            cacodylic acid                                                                            CDAA          CDEC                                                CGA 82725   CH-83         chloramben                                          chlorbromuron                                                                             chlorimuron ethyl                                                                           chloroxuron                                         chlorpropham                                                                              chlorsulfuron chlortoluron                                        cinmethylin clethodim     clomazone                                           cloproxydim clopyralid    CMA                                                 cyanzine    cycloate      cycluron                                            cyperquat   cyprazine     cyprazole                                           cypromid    dalapon       dazomet                                             DCPA        desmediphan   desmetryn                                           diallate    dicamba       dichlorbenil                                        dichlorprop dichlofop     diethatyl                                           difenzoquat dinitramine   dinoseb                                             diphenamid  dipropetryn   diquat                                              diuron      DNOC          DOWCO453ME                                          DPX-M6316   DSMA          endothall                                           EPTC        ethalfluralin ethoxfumesate                                       Express     fenac         fenoxaprop ethyl                                    fenuron     fenuron TCA   flamprop                                            fluazifop   fluazifop-butyl                                                                             fluazifop-P                                         fluchloralin                                                                              fluometuron   fluorochloridone                                    fluorodifen fluoroglycofen                                                                              fluridone                                           fomesafen   fosamine      glyphosate                                          haloxyfop   harmoney      hexaflurate                                         hexazinone  HW-52         imazamethabenz                                      imazapyr    imazaquin     imazethapyr                                         ioxynil     isopropalin   isoproturon                                         isouron     isoxaben      karbutilate                                         lactofen    lenacil       linuron                                             MAA         MAMA          MCPA                                                MCPB        mecoprop      mefluidide                                          methalpropalin                                                                            methabenzthiazuron                                                                          metham                                              methazole   methoxuron    metolachlor                                         metribuzin  metsulfuron methyl                                                                          MH                                                  molinate    monolinuron   monuron                                             monuron TCA MSMA          My-93                                               napropamide naproanilide  naptalam                                            neburon     nitralin      nitrofen                                            nitrofluorfen                                                                             norea         norfluazon                                          NTN-801     oryzalin      oxadiazon                                           oxyfluorfen paraquat      pebulate                                            pendimethalin                                                                             perfluidone   phenmedipham                                        picloram    PPG-1013      pretilachlor                                        procyazine  profluralin   prometon                                            prometryn   pronamide     propachlor                                          propanil    propazine     propham                                             prosulfalin prynachlor    pyrazon                                             pyrazolate  quizalofop ethyl                                                                            quizalofop                                          SC-2957     secbumeton    sethoxydim                                          siduron     simazine      SL-49                                               sulfometuron methyl                                                                       TCA           tebuthiuron                                         terbacil    terbuchlor    terbuthylazine                                      terbutol    terbutryn     thiameturon methyl                                  thiobencarb triallate     triclopyr                                           tridiphane  trifluralin   trimeturon                                          2,4-D       2,4-DB        vernolat                                            X-52        xylachlor                                                         ______________________________________                                    

EXAMPLE 1 2-Fluoro-3-fluoroacetyl pyridine

To a stirring solution of 1.5M lithium diisopropylamide mono(tetrahydrofuran) (69 ml) in 50 ml anhydrous tetrahydrofuran cooled to-70° C. under nitrogen atmosphere is added dropwise 2-fluoropyridine (10g).

To the solution is added dropwise ethyl fluoroacetate (13 g) in 5 ml ofanhydrous tetrahydrofuran at -70° C. and stirred for 3 hours at -70° C.

The reaction mixture is then poured into 200 ml of cold water andneutralized with dilute H₂ SO₄. The mixture is extracted three timeswith methylene chloride. The methylene chloride portions are combined,dried over magnesium sulfate, filtered and evaporation of the methylenechloride, a residue is obtained. This is chromatographed through silicagel using 1:3 ethyl acetatehexane as eluant.

Evaporation of the solvent mixture yields 12 g of the desired product(Yield: 74%).

¹ HNMR (CDCl₃): δ 5.1(s, 1H), 5.8(s, 1H), 7.4(m, 1H), 8.4(m, 2H).

EXAMPLE 2 2-Fluoro-3-(2-fluoro-1-hydroxyethyl)pyridine

To 12 g of 2-fluoro-3-(fluoroacetyl)pyridine dissolved in 30 ml ofmethanol is added dropwise 1.44 g of sodium borohydride. After stirringat 0° C. for 30 minutes to the solution is added 40 ml of water.

The resulting solution is extracted three times with methylene chlorideand the methylene chloride phase is dried over magnesium sulfate,filtered and evaporated to obtain 12 g of the desired product (colorlessoil, Yield: 98%).

EXAMPLE 3 3-(2-Fluoro-1-hydroxyethyl)-2-(phenylmethylthio)pyridine

To a stirring solution of a 60% dispersion of sodium hydride in mineraloil (3.9 g) in 200 ml anhydrous dimethylformamide cooled to -5° C. undernitrogen atmosphere is added 11.6 ml of benzyl mercaptan by using asyringe at a temperature of <0° C.

After stirring at room temperature for one hour a solution of2-fluoro-3-(2-fluoro-1-hydroxyethyl)pyridine (12 g) in 4 ml of anhydrousdimethylformamide is slowly injected at 5° C. The resulting mixture iswarmed slowly to room temperature and stirred for 24 hours.

Water (200 ml) is then added and the mixture is extracted three timeswith Et₂ O. The organic phase is washed with cold water and dried withmagnesium sulfate.

The solvent is removed under reduced pressure, and the residue ischromatographed on silica gel(n-hexane/EtoAc=5:1) to afford the desiredproduct (16 g, oil).

¹ H NMR(CDCl₃): δ 3.4(m, 1H), 3.9-4.3(m, 1H), 4.6(s, 2H), 4.7-5.1(m,1H), 5.2-5.6(m, 1H), 7.0-7.6(m, 6H), 7.9(m, 1H), 8.6(m, 1H).

EXAMPLE 4 3-(1-Acetoxy-2-fluoroethyl)-2-(phenylmethylthio)pyridine

A solution of 3-(2-fluoro-1-hydroxyethyl)-2-(phenylmethylthio)pyridine(16 g) in dry THF and acetic anhydride (7.4 g) is stirred with acatality amount of4-dimethylaminopyridine at room temperature for 12hours. The reaction mixture is then poured into water and neutralizedwith dilute H₂ SO₄. The mixture is extracted three times with methylenechloride, the combined extracts are dried (MgSO₄), evaporated to obtainthe desired product (oil, 17.2 g, Yield: 93%).

¹ H NMR(CDCl₃): δ 2.2(s, 3H), 4.2(d, 1H), 4.5(s, 2H), 5.0(d, 1H), 6.1,6.4(m, 1H) 7.0˜7.8(m, 7H), 8.4(m, 1H).

EXAMPLE 5 3-(1-Acetoxy-2-fluoroethyl)-2-pyridinesulfonamide

To a stirred solution of3-(1-acetoxy-2-fluoroethyl)-2-(phenylmethylthio) pyridine (21 g) in 350ml of methylene chloride and 350 ml of water is added at 0° C. 10.5 mlof conc. HCl.

To the reaction mixture 175 ml of 10% sodium hypochlorite solution isadded for 30 minutes keeping the temperature below 1° C.

The mixture is stirred at 0° C. for 20 minutes, poured into 80 ml ofcold water and extracted three times with cold methylene chloride. Theorganic phase is separated, washed with sodium bisulfite and dried withmagnesium sulfate keeping the temperature below 0° C. The dried solutionis cooled in a dry ice-acetone bath (-70° C.) and then a slow stream ofammonia gas is passed for 10 minutes. The mixture is evaporated untilthe volume of the solution reaches 100 ml.

To the concentrated solution 50 ml of water is add and the mixture isextracted three times with methylene chloride. The combined organiclayer is dried with magnesium sulfate. The solvent is removed underreduced pressure and the residue is chromatographed on silica gel toafford the product (12 g, Yield: 67%).

m.p.: 127°-129° C.

¹ H NMR(DMSO-d6): δ 2.2(s, 3H), 4.3(m, 1H), 5.2(m, 1H), 6.7, 7.1(m, 1H),7.2(s, 2H), 7.7(m, 1H), 8.0(m, 1H), 8.6(m, 1H).

EXAMPLE 6 3-(1-Acetoxy-2-fluoroethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-pyridinesulfonamide

To 4.1 g of 3-(1-acetoxy-2-fluoroethyl)-2-pyridinesulfonamide in 50 mlof acetonitrile is added 4.22 g ofphenyl(4,6-dimethoxypyrimidin-2-yl)carbamate and 2.4 g of1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). After stirring at roomtemperature for 2 hours the solution is acidified to pH 4.5 with 5%hydrochloric acid. The resultant solution is extracted with methylenechloride and the methylene chloride phase is dried over magnesiumsulfate, filtered and evaporated. Trituration of the residue with Et₂ Oyields 6 g of the product (solid, Yield: 89%), which is washed with amixture solvent of ethylacetate/n-hexane(1/1).

m.p.: 145°-147° C.

¹ H NMR (CDCl₃): δ 2.2(s, 3H), 4.0(s, 6H), 4.5 (m, 1H), 5.3(m, 1H),5.8(s, 1H), 6.8-7.2(m, 1H), 7.6(m, 1H), 8.3(m, 1H), 8.7(m, 1H), 13.0(ls,1H).

EXAMPLE 7N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(2-fluoro-1-hydroxyethyl)-2-pyridinesulfonamide

To 4 g of3-(1-acetoxy-2-fluoroethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-pyridinesulfonamidein 100 ml of methanol is added 0.46 g of lithium hydroxide monohydrateand 1 ml of water.

After stirring at room temperature for 3 hours the solution is acidifiedto pH 4.5 with 5% hydrochloric acid. The resultant solution is extractedthree times with methylene chloride. The organic phase is washed threetimes with water, dried over magnesium sulfate, filtered and evaporatedto yield 3.3 g of the subject compound (Yield:90%).

m.p.: 119°-120° C.

¹ H NMR(Acetone-d₆): δ 3.97(s, 6H), 4.38-4.91(m, 2H), 5.36(s, 1H),5.91(s, 1H), 6.03(m, 1H), 7.74(m, 1H), 8.43(m, 1H), 8.57(m, 1H), 9.55(s,1H), 13.02(s, 1H)

EXAMPLE 8 2-(1-Acetoxy-2-fluoroethyl)-3-pyridinesulfonamide

5.3 g of 2-(1-acetoxy-2-fluoroethyl)-N-t-butyl-3-pyridinesulfonamide isadded to 20 ml of trifluoroacetic acid and allowed to stir at roomtemperature for 12 hours. The acid is evaporated and the residual oil istaken up in CH₂ Cl₂. The solution is washed with sat. aq. NaHCO₃, dried(MgSO₄), evaporated and the crude solid product is crystallized fromethyl acetate and n-haxane; 3.1 g (Yield: 71%).

m.p.: 141°-143° C.

¹ HNMR(CDCl₃ +DMSO-d₆): δ 2.13(s, 3H), 4.83(m, 2H), 6.63-7.06(m, 1H),7.20(s, 2H), 7.42-7.63(m, 1H), 8.32-8.86(m, 2H), IR(KBr) 1717 cm⁻¹ (C═O)

EXAMPLE 92-(1-Acetoxy-2-fluoroethyl)-N-[(4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl]-3-pyridinesulfonamide

To a solution of 2-(1-acetoxy-2-fluoroethyl)-3-pyridinesulfonamide (2.10g) and phenyl(4,6-dimethoxypyrimidin-2-yl)carbamate (1.49 g) in 50 mlacetonitrile is added dropwise 0.7 ml of1,8-diazabicyclo[5.4.0]undec-7-ene(DBU) at 15° C. After stirring for 2hours the resultant solution is extracted with methylene chloride and 5%hydrochloric acid. The organic phase is dried over magnesium sulfate,filtered and evaporated to yield the subject compound.

m.p.: 188°-190° C.

¹ HNMR(CDCl₃): δ 2.03(s, 3H), 4.00(s, 6H), 4.84(dd, J₁ =46.0Hz, J₂=6.0Hz, 2H), 5.84(s, 1H), 6.50-6.90(m, 1H), 7.33-7.68(m, 2H),8.60-8.93(m, 2H), 13.33(s, 1H) IR(KBr): 1737, 1702 cm⁻¹ (C═O)

EXAMPLE 102-(2-Fluoro-1-hydroxyethyl)-N-[(4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl]-3-pyridinesulfonamide

To 0.88 g of2-(1-acetoxy-2-fluoroethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-pyridinesulfonamidein 20 ml of methanol is added 0.25 g of lithium hydroxide monohydrate.The mixture is heated to reflux for 1 hour, then allowed to cool and themethanol is evaporated.

The residue is taken up in 15 ml of CH₂ Cl₂ and 10 ml of water, andacidified to pH 2-3 with 1N HClaq. The organic phase is dried overmagnesium sulfate, filtered and evaporated to yield 0.42 g of thesubject compound.

m.p.: 162°-164° C.

¹ HNMR(CDCl₃ +DMSO-d₆): δ 4.02(s, 6H), 4.78(dd, J₁ =46.0Hz, J₂ =5.0Hz,2H), 5.88(s, 1H), 7.53-7.73(m, 1H), 8.53-8.98(m, 2H). IR(KBr): 1704 cm⁻¹(C═O)

EXAMPLE 11 3-(Chloroacetyl)-N-(1,1-dimethylethyl)-2-pyridinesulfonamide

Under a nitrogen atmosphere, to a stirred solution ofN-(1,1-dimethylethyl)-2-pyridinesulfonamide(4.0 g, 18.7 mmole) in 50 mlof anhydrous THF is slowly injected at -70° C. 17 ml of 2.5M n-BuLi.

The mixture is stirred for 3 hours at -40° C., cooled to -70° C. andthen 3 g of ethyl chloroacetate is injected dropwise.

The reaction mixture is stirred at -40° C. for 1 hour, poured into coldwater and extracted three times with CH₂ Cl₂. The organic phase is driedover magnesium sulfate, filtered and evaporated.

The residue is purified by chromatography to give the pure product (3.68g, Yield: 68%).

NMR(CDCl₃): δ 1.2(s, 9H), 4.67(s, 2H), 5.3(s, 1H), 7.8(m, 2H), 9.0(m,1H)

EXAMPLE 123-(2-Chloro-1-hydroxyethyl)-N-(1,1-dimethylethyl)-2-pyrimidinesulfonamide

To a stirred solution of3-(chloroacetyl)-N-(1,1-dimethylethyl)-2-pyridinesulfonamide (3.68 g,12.7 mmole) in 100 ml of methanol is added at 0° C. NaBH₄ (0.24 g, 6.35mmole). The reaction mixture is stirred at 0° C. for 1 hour, added 10 mlof water and extracted three times with CH₂ Cl₂.

The organic phase is dried over magnesium sulfate, filtered andevaporated to yield 3.56 g of the subject compound (Yield: 96%).

EXAMPLE 133-(1-Acetoxy-2-chloroethyl)-N-(1,1-dimethylethyl)-2-pyrimidinesulfonamide

To a stirred solution of3-(2-chloro-1-hydroxyethyl)-N-(1,1-dimethylethyl)-2-pyridinesulfonamidein dry THF is added 1.6 g of Ac₂ O and a catality amount of4-dimethylaminopyridine. The mixture is stirred at room temperature for12 hours, water is added, neutralized with dilute H₂ SO₄ and extractedthree times with CH₂ Cl₂. The organic phase is evaporated to give thesubject compound (3.6 g, Yield: 88%).

NMR(CDCl₃): δ 1.2(s, 9H), 2.2(s, 3H), 4.0(m, 2H), 5.7(s, 1H), 7.0(m,1H), 7.7(m, 1H), 8.1(m, 1H), 8.7(m, 1H).

EXAMPLE 14 3-(1-Acetoxy-2-chloroethyl)-2-pyridinesulfonamide

3.6 g of3-(1-acetoxy-2-chloroethyl)-N-(1,1-dimethylethyl)-2-pyridinesulfonamideis added to 20 ml of trifluoroacetic acid and allowed to stir at 40° C.for 12 hours. The acid is evaporated and the crude product is purifiedby column chromatography to give the subject compound (3 g).

m.p.: 146°-147° C.

NMR(CDCl₃): δ 2.1(s, 3H), 4.0(m, 2H), 6.0(s, 2H), 6.9(m, 1H), 7.7(m,1H), 8.1(m, 1H), 8.7(m, 1H)

EXAMPLE 153-(1-Acetoxy-2-chloroethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-pyridinesulfonamide

To a stirred solution of3-(1-acetoxy-2-chloroethyl)-2-pyridinesulfonamide (200 mg) andphenyl(4,6-dimethoxypyrimidin-2-yl)carbamate (197 mg) in 20 ml ofacetonitrile is added dropwise 109 mg of DBU.

After stirring at room temperature for 2 hours the solution is acidifiedto pH 4.5 with 5% aq. HCl. The resultant solution is extracted threetimes with methylene chloride and the methylene chloride phase is driedover MgSO₄, filtered and evaporated.

Trituration of the residue with Et₂ O (10 ml) yield 280 mg of the solidproduct.

m.p.: 159°-161° C.

EXAMPLE 163-(2-Chloro-1-hydroxyethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-pyridinesulfonamide

To 140 mg of3-(1-acetoxy-2-chloroethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-pyridinesulfonamidein 20 ml of methanol is added 20 mg of LiOH.H₂ O and 0.5 ml of water.After stirring at room temperature for 3 hours the solution is acidifiedto pH 4.5 with 5% aq. HCl. The resultant solution is extracted threetimes with CH₂ Cl₂. The organic phase is evaporated and the triturationof the residue with Et₂ O yields the solid product.

m.p.: 135°-137° C.

In the following example, all parts are by weight unless otherwiseindicated.

EXAMPLE 17

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N-[(4,6-dimethoxy pyrimidin-2-yl)amino carbonyl]-                                                          80%                                              3-(2-fluoro-1-hydroxyethyl)-2-pyridinesulfonamide                             sodium alkylnaphthalenesulfonate                                                                           2%                                               sodium ligninsulfonate       2%                                               synthetic amorphous silica   3%                                               kaolinite                    13%                                              ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids areessentially under 50 microns, reblended, and packaged.

EXAMPLE 18

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        3-(2-fluoro-1-hydroxyethyl)-N-[(4-methoxy-6-methyl-                                                        50%                                              pyrimidin-2-yl) amino carbonyl]-2-pyridine sulfonamide                        sodium alkylnaphthalenesulfonate                                                                           2%                                               low viscosity methyl cellulose                                                                             2%                                               diatomaceous earth           46%                                              ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles essentially all below 10 microns in diameter. Theproduct is reblended before packaging.

EXAMPLE 19

    ______________________________________                                        Granule                                                                       ______________________________________                                         2                                                                            wettable powder of Example 18                                                                              5%                                               attapulgite granules(U.S.S. 20-40 mesh; 0.84˜0.42                                                    95%                                              ______________________________________                                    

A slurry of wettable powder containing 25% solids is sprayed on thesurface of attapulgite granules in a double-cone blender.

The granules are dried and packaged.

EXAMPLE 20

    ______________________________________                                        Extruded Pellet                                                               ______________________________________                                        N-[(4,6-dimethoxypyrimidin-2-yl)amino carbonyl]-                                                           25%                                              3-(2-fluoro-1-hydroxyethyl)-2-pyridinesulfonamide                             anhydrous sodium sulfate     10%                                              crude calcium lignisulfonate 5%                                               sodium alkylnaphthalenesulfonate                                                                           1%                                               calcium/magnesium bentonite  59%                                              ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. They may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 21

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        N-[(4,6-dimethoxy pyrimidin-2-yl)amino carbonyl]-                                                          25%                                              3-(2-fluoro-1-hydroxyethyl)-2-pyridinesulfonamide                             polyoxyethylene sorbitol hexaoleate                                                                        5%                                               highly aliphatic hydrocarbon oil                                                                           70%                                              ______________________________________                                    

The ingredients are ground together in sand mill until the solidparticles have been reduced to under about 5 microns. The resultingthick suspension may be applied directly, but preferably after beingextended with oils or emulsified in water.

EXAMPLE 22

    ______________________________________                                        Wetting Powder                                                                ______________________________________                                        N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                            20%                                              3-(2-fluoro-1-hydroxyethyl)-2-pyridinesulfonamide                             sodium alkylnaphthalenesulfonate                                                                           4%                                               sodium ligninsulfonate       4%                                               low viscosity methyl cellulose                                                                             3%                                               attapulgite                  69%                                              ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-millto produce particles essentially all below 100 microns, the material isreblended and sifted through a U.S.S. No. 50 sieve (0.3 mm openings) andpackaged.

EXAMPLE 23

    ______________________________________                                        Low Strength Granule                                                          ______________________________________                                        N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                            1%                                               3-(2-fluoro-1-hydroxyethyl)-2-pyridinesulfonamide                             N,N-dimethylformamide        9%                                               attapulgite granule (U.S.S. 20-40 sieve)                                                                   90%                                              ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a double cone blender.

After spraying of the solution has been completed, the blender isallowed to run for a short period and then the granules are packaged.

EXAMPLE 24

    ______________________________________                                        Aqueous Suspension                                                            ______________________________________                                        N-[(4,6-dimethoxy pyrimidin-2-yl)aminocarbonyl]-                                                          40%                                               3-(2-fluoro-1-hydroxyethyl)-2-pyridinesulfonamide                             polyacrylic acid thickener  0.3%                                              dodecylphenol polyethylen glycol ether                                                                    0.5%                                              disodium phosphate          1%                                                monosodium phosphate        0.5%                                              polyvinyl alcohol           1%                                                water                       56.7%                                             ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 25

    ______________________________________                                        Solution                                                                      ______________________________________                                        N-[(4,6-dimethoxy pyrimidin-2-yl)aminocarbonyl]-3-(2-                                                      5%                                               fluoro-1-hydroxyethyl)-2-pyridinesulfonamide, ammonium                        salt                                                                          water                        95%                                              ______________________________________                                    

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for use.

EXAMPLE 26

    ______________________________________                                        Low Strength Granule                                                          ______________________________________                                        N-[(4,6-dimethoxy pyrimidin-2-yl)aminocarbonyl]-                                                          0.1%                                              3-(2-fluoro-1-hydroxyethyl)-2-pyridinesulfonamide                             attapulgite granules (U.S.S. No. 20-140 mesh)                                                             99.9%                                             ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution issprayed upon dedusted granules in a double-cone blender. After sprayingof the solution has been completed, the material is warmed to evaporatethe solvent. The material is allowed to cool and packaged.

EXAMPLE 27

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N-[(4,6-dimethoxy pyrimidin-2-yl)aminocarbonyl]-                                                           40%                                              3-(2-fluoro-1-hydroxyethyl)-2-pyridinesulfonamide                             dioctyl sodium sulfosuccinate                                                                              1.5%                                             sodium ligninsulfonate       3%                                               low viscosity methyl cellulose                                                                             1.5%                                             attapulgite                  54%                                              ______________________________________                                    

The ingredient are thoroughly blended, passed through an air mill, toproduce an average particle size under 15 microns, reblended, and siftedthrough a U.S.S. No. 50 sieve (0.3 mm opening) before packaging. Allcompounds of the invention may be formulated in the same manner.

EXAMPLE 28

    ______________________________________                                        Granule                                                                       ______________________________________                                        wettable powder of Example 18                                                                           15%                                                 gypsum                    69%                                                 potassium sulfate         16%                                                 ______________________________________                                    

The ingredients are blended in rotating mixer and water sprayed on toaccomplish granulation. When most of the material has reached thedesired range of 1.0 to 0.42 cm (U.S.S. #18 to 40 sieves), the granulesare removed, dried, and screened. Oversized material is crushedadditional material in the desired range. These granules contain %active ingredient.

EXAMPLE 29

    ______________________________________                                        High Strength Concentrate                                                     ______________________________________                                        N-[(4,6-dimethoxy pyrimidin-2-yl)aminocarbonyl]-                                                           99%                                              3-(2-fluoro-1-hydroxyethyl)-2-pyridinesulfonamide                             silica aerogel               0.5%                                             synthetic amorphous silica   0.5%                                             ______________________________________                                    

The ingredient are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 30

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        3-(2-fluoro-1-hydroxyethyl)-N-[(4-methoxy-6-methyl-                                                        90%                                              pyrimidin-2-yl) aminocarbonyl]-2-pyridinesulfonamide                          dioctyl sodium sulfosuccinate                                                                              0.1%                                             synthetic fine silica        9.9%                                             ______________________________________                                    

The ingredient are blended and ground in a hammer-mill to produceparticles essentially all below 100 microns. The material is siftedthrough a U.S.S. No. 50 screen and the packaged.

EXAMPLE 31

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        N-[(4,6-dimethoxy pyrimidin-2-yl)aminocarbonyl)-                                                           40%                                              3-(2-fluoro-1-hydroxyethyl)-2-pyridinesulfonamide                             sodium ligninsulfonate       20%                                              montmorillonite clay         40%                                              ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and the packaged.

EXAMPLE 32

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        N-[(4,6-dimethoxy pyrimidin-2-yl)aminocarbonyl)-                                                           35%                                              3-(2-fluoro-1-hydroxyethyl)-2-pyridinesulfonamide                             blended of polyalcohol carboxylic estes and oil                                                            6%                                               soluble petroleum                                                             xylene                       59%                                              ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particle essentially all below 5 microns. The product can beused directly, extended with oil, or emulsified in water.

EXAMPLE 33

    ______________________________________                                        Dust                                                                          ______________________________________                                        N-[(4,6-dimethoxy pyrimidin-2-yl),aminocarbonyl)-                                                          10%                                              3-(2-fluoro-1-hydroxyethyl)-2-pyridinesulfonamide                             attapulgite                  10%                                              pyrophyllite                 80%                                              ______________________________________                                    

The active ingredient is blended with attapulgite and then passedthrough a hammer-mill to produce particles substantially all below 200microns. The ground concentrate is then blended with powderedpyrophyllite until homogeneous.

EXAMPLE 34

    ______________________________________                                        Emulsifiable Concentrate                                                      ______________________________________                                        N-[(4,6-dlmethoxypyrimidin-2-yl)aminocarbonyl)-                                                            10%                                              3-(2-fluoro-1-hydroxyethyl)-2-pyridinesulfonamide                             chlorobenzene                84%                                              sorbitan monostearate and polyoxyethylene                                                                  6%                                               condensates thereof                                                           ______________________________________                                    

The ingredients are combined and stirred to produce a solution which canbe emulsified in water for application.

EXAMPLE 35

Pre-emergence test

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with 5 parts by weight of acetone, 1 part byweight of alkylaryl polyglycol ether of emulsifier is added and theconcentrate is diluted with water to the desired concentration.

Seeds of the test plants are shown in normal soil and, after 24 hours,watered with the preparation of the active compound.

It is expedient to keep constant the amount of water per unit area. Theconcentration of the active compound in the preparation is of noimportance, only the amount of active compound applied per unit areabeing desicive. After three weeks, the degree of damage to the plants israted in % damage in comparison to the development of the untreatedcontrol.

The figures denote:

0%=no action (like untreated control)

20%=slight effect

70%=herbicidal effect

100%=total destruction.

In this test, the active compounds(I) according to the preparationExamples exhibit a better herbicidal activity against nomo- anddicotyledon weeds.

EXAMPLE 36

Post-emergence test

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with 5 pans by weight of acetone, 1 part byweight of alkylaryl polyglycol ether of emulsifier is added and theconcentrate is diluted with water to the desired concentration.

Test plants which have a height of 5˜15 cm are sprayed with thepreparation of the active compound in such a way as to apply theparticular amounts of active compound desired per unit area. Theconcentration of the spray liquor is so chosen that the particularamounts of active compound desired are applied in 2,000 l of water/ha.After three weeks, the degree of damage to the plants is rated in %damage in comparasion to the development of the untreated control.

The figures denote:

0%=no action (like untreated control)

20%=slight effect

70%=herbicidal effect

100%=total destruction.

In this test, the active compounds(I) according to the preparationExamples exhibit a better herbicidal activity against mono- anddicotyledon weeds.

It is understood that the specification and examples are illustrativebut not limitative of the present invention and that other embodimentswithin the spirit and scope of the invention will suggest themselves tothose skilled in the art.

The herbicidal proficiency of the active ingredients of the presentinvention is evident from the test results which are recorded infollowing Table 29.

The following Table 29 below is represented pre- and post-emergenceherbicidal evaluation [PRIMARY SCREENING (Herbicide)] of following "testcompounds".

    __________________________________________________________________________    Structure                 X          Y   Compound No.                         __________________________________________________________________________     ##STR75##                                                                                               ##STR76##                                                                                ##STR77##                                                                         ##STR78##                            ##STR79##                                                                                               ##STR80##                                                                                ##STR81##                                                                         ##STR82##                            ##STR83##                                                                                               ##STR84##                                                                                ##STR85##                                                                         ##STR86##                            ##STR87##                                                                                               ##STR88##                                                                                ##STR89##                                                                         ##STR90##                            ##STR91##                                                                                               ##STR92##                                                                                ##STR93##                                                                         ##STR94##                            ##STR95##                                                                                               ##STR96##                                                                                ##STR97##                                                                         ##STR98##                           __________________________________________________________________________    PLANT RESPONSE SCREENING (Herbicide)                                          Com-                  BROJA                                                   pound                 (SETVI)                                                 no. TYPE                                                                              kg/ha                                                                             SORBI                                                                              ECHOR                                                                              [AGRSM]                                                                             DIGSA                                                                              PANDI                                                                              SOLNI                                                                              AESIN                                                                              ABUTH                                                                              XANSI                                                                              CAGHE               __________________________________________________________________________     1  PRE .05 100  100  100   100  100  50   90   100  100  100                     POST                                                                              .05 100  100  100   100  100  50   100  100  100  100                  2  PRE .05 100  100  (100) 100  100       30   80   90   100                     POST                                                                              .05 100  100  (100) 100  100  20   100  90   100  100                  3  PRE .05 90   60   [0]   50   100  0    0    0    0    85                      POST                                                                              .05 90   100  [70]  90   100  60   25   20   50   70                   4  PRE .05 100  100  [90]  100  100  100  80   90   90   100                     POST                                                                              .05 100  100  [100] 100  100  70   100  90   100  100                  5  PRE .05 100  100  [50]  100  100  65   30   90   85   100                     POST                                                                              .05 100  100  [60]  100  100  60   90   85   100  100                  6  PRE 4   100  100  [100] 100  100  100  100  90   100  100                     POST                                                                              4   100  100  [ 100]                                                                              100  100  100  100  100  100  100                  7  PRE 4   100  100  [90]  100  100  100  90   100  90   100                     POST                                                                              4   100  100  [100] 100  100  100  100  100  100  100                  8  PRE 4   100  100  [90]  100  100  100  100  90   90   100                     POST                                                                              4   100  100  [100] 100  100  100  100  100  100  100                  9  PRE 4   100  100  [100] 100  100  100  100  90   90   100                     POST                                                                              4   100  100  [100] 100  100  100  100  100  100  100                 10  PRE 4   100  100  [90]  100  100  100  90   90   90   100                     POST                                                                              4   100  100  [100] 100  100  100  100  90   100  100                 11  PRE .05 100  90   [70]  95   90   30   40   75   90   100                     POST                                                                              .05 60   100  [50]  60   80   0    90   65   90   85                  12  PRE .05 100  100  [90]  95   100  80   65   80   85   100                     POST                                                                              .05 100  100  [80]  100  100  40   100  80   100  60                  13  PRE .05 90   70   [20]  50   90   90   0    25   60   60                      POST                                                                              .05 70   65   [15]  0    60   30   20   0    70   60                  14  PRE 4   100  100  [90]  100  100  100  100  90   100  100                     POST                                                                              4   100  100  [100] 100  100  100  100  100  100  100                 15  PRE 4   100  100  [90]  100  100  100  100  90   90   100                     POST                                                                              4   100  100  [100] 100  100  100  100  100  100  100                 16  PRE 4   100  90   [90]  100  100  100  70   90   90   100                     POST                                                                              4   100  100  [80]  100  100  100  100  90   100  100                 17  PRE 4   100  100  [90]  100  100  100  90   90   90   100                     POST                                                                              4   100  100  [90]  100  100  100  100  100  100  100                 18  PRE 4   90   90   [70]  100  100  100  85   90   90   100                     POST                                                                              4   100  100  [70]  100  100  100  90   80   90   100                 19  PRE .05 100  100  [90]  100  100  70   30   80   90   95                      POST                                                                              .05 100  100  [70]  65   100  30   100  70   100  70                  20  PRE .05 100  90   [80]  100  90   60   20   60   90   100                     POST                                                                              .05 90   100  [65]  60   90   10   65   30   80   70                  21  PRE .05 100  80   [60]  65   50   30   0    0    45   70                      POST                                                                              .05 100  80   [0]   0    65   20   0    0    35   20                  22  PRE .05 100  100  [50]  100  100  60   50   85   90   100                     POST                                                                              .05 100  100  [40]  100  100  60   100  90   90   90                  23  PRE .05 90   90   [40]  100  100  60   50   90   90   100                     POST                                                                              .05 90   65   [55]  60   60   30   80   85   90   85                  24  PRE .05 0    0    [0]   15   50   0    0    10   0    0                       POST                                                                              .05 0    0    [0]   0    0    0    0    0    0    0                   25  PRE .05 0    0    [0]   0    0    0    0    0    0    65                      POST                                                                              .05 0    0    [0]   0    0    0    0    0    0    10                  26  PRE .05 20   10   [0]   0    0    0    0    0    0    0                       POST                                                                              .05 0    0    [0]   0    0    0    0    0    0    0                   __________________________________________________________________________

      PRIMARY SCREENING (Herbicide)           BROJA        Compound     (SETVI) No. TYPE kg/ha ZEAMX GLXMX GOSHI TRZAW ORYSA SORBI ECHOR [AGRSM]     DIGSA PANDI SOLNI AESIN ABUTH XANSI CAGHE       1 PRE .1 100 100 100 100 100 100 100 (100) 100 100 70 70 100 100 100     .05 100 100 100 100 100 100 100 (100) 100 100 40 60 100 100 100   .025     70 100 100 100 100 100 100 (100) 100 100 0 40 90 100 100   .0125 60 100     70 100 100 100 100 (100) 100 100 0 30 80 70 100   .00625 40 70 40 65 100     100 90 (100) 100 100 0 0 60 70 100   .025 80 100 70 100 100 100 100 (90)     100 100 50 65 90 100 100   .0125 70 90 70 90 100 100 90 (85) 100 100 40     40 80 90 100   .00625 40 80 50 80 100 100 85 (80) 100 100 40 30 70  100      .003125 0 65 50 75 100 90 80 (70) 100 100 30 20 70 100   .00151 0 50 40     40 70 80 70 (70) 100 100 30 0 50  60 1 POST .1 100 100 100 100 100 100     100 (100) 100 100  100 100 100 100   .05 100 100 90 100 100 100 100     (100) 100 100  100 100 100 100   .025 100 100 70 100 100 100 100 (100)     100 100  100 100 100 100   .0125 70 100 60 80 100 100 100 (100) 100 100     90 100 100 90   .00625 30 100 20 70 100 100 100 (100) 100 100  60 80 70     80   .025 80 100 60 90 90 100 100 (100) 100 100 40 100 100 100 100     .0125 70 100 50 90 95 100 100 (100) 100 100 40 100 100 100 100   .00625     60 100 30 65 90 100 100 (100) 100 90 20 100 100 100 100   .003125 0 30     75 0 60 90 100 (90) 90 80 0 60 60 95 65   .00151 0 70 0 50 70 100 100     (80) 90 80 0 50 50 65 65 2 PRE .1 80 100 50 100 100 100 80 (90) 100 100     40 60 70 90 100   .025 50 90 40 90 100 100 95 (80) 100 100 20 20 40 90     100   .006 0 60 0 50 90 80 75 (70) 95 100 0 0 20 40 100   .0015 0 20 0 0     30 20 50 (30) 80 90 0 0 0 0 100  POST .1 65 100 50 60 70 100 100 (100)     100 90 70 80 100 100 100   .025 60 100 10 40 80 60 100 (90) 100 90 30 60     60 100 100   .006 30 70 0 40 80 50 90 (90) 80 90 10 40 60 90 90   .0015     0 60 0 40 60 40 60 (90) 70 30 10 20 40 60 60 4 PRE .1 80 100 100 100 100     100 100 [90] 100 100 80 65 100 100 100   .025 70 70 80 100 100 100 100     [70] 100 100 60 10 65 70 100   .006 30 30 50 60 100 100 70 [40] 100 100     20 0 20 40 100   .00156 0 0 0 0 50 60 30 [0] 40 70 0 0 0 0 20   .00039 0     0 0 0 0 0 0 [0] 0 0 0 0 0 0 0  POST .1 100 100 70 100 100 100 100 [100]     100 100 60 70 90 100 100   .025 50 100 20 100 100 100 100 [70] 100 100     60 60 70 100 100   .006 0 100 0 50 100 70 100 [60] 100 100 30 20 40 50     80   .00156 0 40 0 0 70 70 80 [20] 70 70 0 0 0 30 40   .00039 0 0 0 0 0     30 50 [0] 0 65 0 0 0 0 0 5 PRE .1 100 100 90 100 100 100 100 [100] 100     100 60 30 70 100 100   .025 20 30 20 65 100 100 90 [50] 100 100 20 0 20     50 50   .006 0 0 0 20 70 100 20 [0] 20 90 0 0 0 0 30   .00156 0 0 0 0 10     20 0 [0] 0 40 0 0 0 0 0   .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0  POST     .1 90 100 40 100 100 100 100 [50] 100 100 50 70 60 90 100   .025 30 90 0     90 100 100 100 [40] 100 100 40 40 50 80 60   .006 10 60 0 30 60 60 70     [0] 30 90 0 20 0 70 30   .00156 0 40 0 0 0 0 0 [0] 0 60 0 0 0 0 0     .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0 6 PRE .1 100 100 100 100 100 100     100 [100] 100 100 70 100 100 100 100   .025 100 100 100 100 100 100 100     [100] 100 100 60 30 100 100 100   .00625 100 60 70 70 100 100 100 [60]     100 100 40 0 50 90 80   .001562 40 30 40 30 100 90 60 [0] 80 100 0 0 0     30 30   .00039 0 0 0 0 70 0 0 [0] 0 0 20 0 0 0 0  POST .1 100 100 90 100     100 100 100 [100] 100 100 100 100 100 100 100   .025 100 100 80 100 100     100 100 [100] 100 100 50 100 80 100 100   .00625 100 100 70 90 100 100     100 [70] 100 100 30 60 70 100 60   .001562 40 80 40 30 100 80 80 [30] 60     90 0 0 0 60 50   .00039 0 30 0 0 60 60 40 [0] 0 60 0 0 0 0 20 9 PRE .1     100 70 80 100 100 100 100 [80] 100 100 70 20 60 70 100   .025 60 30 50     60 100 100 100 [40] 100 100 40 0 0 65 60   .00625 20 0 20 30 100 90 70     [0] 30 40 20 0 0 40 30   .001562 0 0 0 0 60 60 20 [0] 0 0 0 0 0 0 0     .00039 0 0 0 0 40 0 0 [0] 0 0 0 0 0 0 0  POST .1 100 100 80 100 100 100     100 [100] 100 100 100 65 60 90 80   .025 50 70 40 40 100 100 100 [80]     100 100 100 40 30 80 90   .00625 40 40 0 20 100 70 50 [30] 40 80 30 0 0     40 30   .001562 0 0 0 0 50 50 20 [0] 0 30 0 0 0 0 0   .00039 0 0 0 0 0     20 0 [0] 0 0 0 0 0 0 0 10 PRE .1 70 0 40 20 100 100 70 [30] 65 80 20 0     30 30 50   .025 20 0 30 0 60 60 20 [0] 20 60 0 0 0 0 0   .00625 0 0 0 0     20 0 0 [0] 0 0 0 0 0 0 0   .001562 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0     .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0  POST .1 50 50 40 30 90 100 60     [30] 30 100 0 40 0 50 50   .025 40 40 30 0 50 70 40 [0] 0 0 0 0 0 20 40      .00625 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0   .001562 0 0 0 0 0 0 0 [0] 0 0     0 0 0 0 0   .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0 11 PRE .1 0 70 60 40     100 70 60 [60] 80 100 20 20 70 80 70   .025 0 10 30 0 65 20 40 [0] 40 50     0 0 0 30 20   .00625 0 0 0 0 20 0 0 [0] 30 0 0 0 0 0 0   .001562 0 0 0 0     0 0 0 [0] 0 0 0 0 0 0 0   .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0  POST     .1 0 100 60 40 90 50 100 [50] 80 70 0 70 50 100 100   .025 0 50 30 10 40     0 30 [0] 0 0 0 20 0 60 50   .00625 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 30     .001562 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0   .00039 0 0 0 0 0 0 0 [0] 0 0 0     0 0 0 0 12 PRE .1 100 100 100 70 100 100 100 [80] 100 100 100 70 100 100     100   .025 70 50 50 30 100 90 80 [30] 50 100 30 10 40 80 65   .00625 20     0 0 0 90 30 20 [0] 20 70 0 0 0 20 20   .001562 0 0 0 0 20 0 0 [0] 0 20 0     0 0 0 0   .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0  POST .1 100 100 80 100     100 100 100 [80] 100 100 60 90 70 100 100   .025 100 90 60 30 100 100     100 [20] 40 100 30 70 40 70 40   .00625 20 50 20 0 70 30 20 [0] 0 30 0     30 0 40 0   .001562 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0   .00039 0 0 0 0 0 0     0 [0] 0 0 0 0 0 0 0 14 PRE .1 100 100 90 100 100 100 100 [100] 100 100     70 80 100 100 100   .025 20 90 80 100 100 100 100 [70] 100 100 40 50 70     90 100   .00625 0 60 50 50 100 100 70 [30] 60 100 0 0 50 80 70   .00156     0 20 0 0 50 50 40 [0] 0 80 0 0 0 30 30   .00039 0 0 0 0 0 0 0 [0] 0 0 0     0 0 0 0  POST .1 90 100 60 100 100 100 100 [90] 100 100 60 100 90 100     100   .025 40 100 40 90 90 100 100 [60] 100 100 50 100 60 100 100     00625 0 80 0 50 90 100 70 [40] 40 90 0 40 50 100 40   .00156 0 60 0 20     50 50 50 [0] 0 90 0 0 0 40 20   .00039 0 30 0 0 20 0 0 [0] 0 60 0 0 0 0     0 15 PRE .1 40 100 70 70 100 100 100 [60] 100 100 30 40 60 80 100   .025     0 60 40 50 100 80 80 [0] 100 90 0 0 20 50 100   .00625 0 20 0 30 40 0 20     [0] 50 80 0 0 0 0 50   .00156 0 0 0 0 0 0 0 [0] 0 20 0 0 0 0 0   .00039     0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0  POST .1 10 100 60 70 100 70 100 [70]     100 100 70 80 50 90 60   .025 0 90 50 50 90 40 90 [30] 50 80 0 50 40 80     40   .00625 0 50 0 20 40 0 60 [0] 0 20 0 20 0 60 30   .00156 0 30 0 0 0     0 0 [0] 0 0 0 0 0 0 0   .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0 16 PRE .1     0 0 0 30 90 90 40 [0] 40 50 40 0 0 0 0   .0250 0 0 0 0 30 40 0 [0] 0 0 0     0 0 0 0   .00625 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0   .001562 0 0 0 0 0 0 0     [0] 0 0 0 0 0 0 0   .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0  POST .1 0 40     40 40 100 60 90 [0] 0 30 30 0 0 60 60   .025 0 10 20 10 50 30 30 [0] 0 0     20 0 0 0 0   .00625 0 0 0 0 0 20 0 [0] 0 0 0 0 0 0 0   .001562 0 0 0 0 0     0 0 [0] 0 0 0 0 0 0 0   .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0 17 PRE .1     0 70 50 60 100 100 100 [50] 100 100 80 0 40 70 70   .025 0 0 20 40 100     90 70 [30] 40 90 40 0 0 40 40   .00625 0 0 0 30 50 30 20 [0] 0 40 20 0 0     0 0   .00156 0 0 0 0 20 0 0 [0] 0 0 0 0 0 0 0   .00039 0 0 0 0 0 0 0 [0]     0 0 0 0 0 0 0  POST .1 20 100 50 60 100 100 100 [50] 100 100 60 40 30 90     40   .025 0 50 30 20 65 60 100 [0] 50 80 40 0 0 60 20   .00625 0 0 0 0     30 20 60 [0] 0 0 0 0 0 20 0   .00156 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0     .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0 19 PRE .1 70 65 70 60 100 100 100     [80] 100 100 80 20 80 100 100   .025 10 20 20 30 100 80 70 [20] 50 100     40 0 40 60 70   .00625 0 0 0 0 70 50 0 [0] 0 70 0 0 0 40 20   .001562 0     0 0 0 0 0 0 [0] 0 0 0 0 0 0 0   .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0     POST .1 70 100 65 100 100 100 100 [80] 100 100 70 70 80 100 100   .025     20 40 40 40 70 100 90 [40] 20 90 40 40 30 80 60   .00625 0 0 0 20 30 40     40 [0] 0 40 30 0 0 0 30   .001562 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0     .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0 20 PRE .1 10 40 30 50 100 100 100     [70] 100 100 60 30 70 100 70   .025 0 10 0 30 80 20 20 [20] 30 30 0 0 10     100 50   .00625 0 0 0 0 40 0 0 [0] 0 0 0 0 0 30 0   .001562 0 0 0 0 0 0     0 [0] 0 0 0 0 0 0 0   .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0  POST .1 0     70 50 60 100 90 100 [50] 50 60 30 70 30 90 70   .025 0 40 30 20 40 40 50     [0] 0 0 0 20 0 40 40   .00625 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0   .001562     0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0   .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0     22 PRE .1 100 100 100 20 100 100 100 [40] 100 100 70 100 100 100 100     .025 100 100 80 0 100 100 100 [30] 90 90 60 60 80 70 100   .00625 90 50     40 0 60 80 80 [0] 50 60 20 20 70 30 30   .001562 30 40 0 0 40 30 20 [0]     0 20 0 0 0 0 20   .00039 0 20 0 0 20 0 0 [0] 0 0 0 0 0 0 0  POST .1 100     100 100 60 100 100 100 [50] 100 100 100 100 100 100 100   .0025 100 100     80 10 50 100 100 [30] 80 100 50 40 70 100 50   .00625 70 70 40 0 30 60     40 [0] 40 40 40 30 60 60 40   .001562 20 40 0 0 0 20 0 [0] 0 0 30 0 0 20     30   .00039 0 0 0 0 0 0 0 [0] 0 0 0 0 0 0 0

    __________________________________________________________________________    PRIMARY SCREENING (PADDY SUBMERGED)-HERBICIDE                                 Compound      ORYSA                                                                              ORYSA                                                      no.   DAT kg/ha                                                                             (3Leaf)                                                                            (seed)                                                                             ECHOR                                                                              SCPJU                                                                             MOOVA                                                                              CYPSE                                                                              SAGPY                              __________________________________________________________________________    1     2   .05 100  100  100  80  90   100  70                                           .1  100  100  100  100 100       100                                          0.25                                                                              100  100  100  100 100       90                                           .006                                                                              90   90   100  50  90        80                                           .0015                                                                             10   10   100  0   70        70                                           .0004                                                                             0    0    20   0   30        50                                 2     2   .05 40   40   50   20  60        60                                 3     2   .05 40   0    20   0   0    40   50                                 4     2   .05 90   70   80   60  90   80   80                                 5     2   .05 60   70   60   0   80   80   80                                 6     2   4   100  100  100  100 100  100  100                                          .05 100  100  90   100 100  100  100                                          .025                                                                              100  100  90   90  90   100  100                                          .0125                                                                             100  100  80   70  70   100  100                                          .0062                                                                             60   50   0    0   0    100  100                                          .003                                                                              20   0    0    0   0    0    20                                 7     2   4   100  100  100  100 100  100  100                                          4   100  100  100  100 100  100  100                                          1   100  100  90   100 100  100  100                                          .25 100  100  90   100 100  100  100                                          .06 100  100  80   100 100  100  100                                          .015                                                                              100  90   80   100 100  100  100                                          .05 100  100  70   0   50   80   100                                          .025                                                                              50   40   40   0   0    30   100                                          .0125                                                                             40   30   X    0   0    50   30                                           .0062                                                                             30   X    0    0   0    X    0                                            .003                                                                              0    0    0    0   0    0    0                                  8     2   4   100  100  100  100 100  100  100                                          4   100  100  100  100 100  100  100                                          1   100  90   80   50  90   100  100                                          .25 100  80   50   20  50   80   90                                           .06 80   60   20   0   0    X    70                                           .015                                                                              0    0    0    0   0    0    0                                  9     2   4   100  100  100  100 100  100  100                                          .05 100  100  70   50  80   100  100                                          .025                                                                              40   60   30   0   30   100  100                                          .0125                                                                             0    0    0    0   0    0    0                                            .0062                                                                             0    0    0    0   0    0    0                                            .003                                                                              0    0    0    0   0    0    0                                        3   .05 80   90   90   60  80   100  100                                          .0125                                                                             0    0    0    0   0    0    0                                            .003                                                                              0    0    0    0   0    0    0                                            .00078                                                                            0    0    0    0   0    0    0                                            .0002                                                                             0    0    0    0   0    0    0                                            .05 50   50   70   0   0    30   0                                            .0125                                                                             0    20   0    0   0    0    0                                            .00312                                                                            0    0    0    0   0    0    0                                            .00078                                                                            0    0    0    0   0    0    0                                            .0002                                                                             0    0    0    0   0    0    0                                  10    2   4   100  100  100  100 100  100  100                                11    2   .05 70   60   70   20  50   70   90                                 12    2   .05 90   90   90   90  90   90   90                                           .05 100  100  100  100 100  100  100                                          .025                                                                              100  100  100  100 100  100  100                                          .0125                                                                             100  100  100  100 100  100  100                                          .006                                                                              100  100  70   100 100  100  100                                          .003                                                                              80   90   50   70  100  100  100                                      3   .05 100  100  100  95  90   100  100                                          .0125                                                                             40   70   40   60  50   70   100                                          .003                                                                              0    0    0    0   0    0    0                                            .00078                                                                            0    0    0    0   0    0    0                                            .0002                                                                             0    0    0    0   0    0    0                                  13    2   .05 70   70   60   50  50   80   70                                 14    2   4   100  100  100  100 100  100  100                                15    2   4   100  10   100  100 100  100  100                                16    2   4   100  100  100  100 100  100  100                                17    2   4   100  100  100  100 100  100  100                                19    2   .05 80   90   80   90  80   80   80                                           .05 100  100  100  80  100  100  100                                          .025                                                                              100  100  90   60  100  100  100                                          .0125                                                                             90   100  70   60  100  100  100                                          .006                                                                              90   70   40   30  100  80   90                                           .003                                                                              60   60   0    0   100  60   70                                 20    2   .05 80   70   60   40  40   60   70                                 21    2   .05 70   60   60   20  30   60   60                                 22    3   .05 60   60   60   90  90   100  90                                       2   .05 0    0    0    40  0    80   100                                          .0125                                                                             0    0    0    0   0    0    0                                            .00312                                                                            0    0    0    0   0    0    0                                            .00078                                                                            0    0    0    0   0    0    0                                            .00019                                                                            0    0    0    0   0    0    0                                  23    3   .05 50   50   20   70  80   100  90                                 24    3   .05 0    0    40   0   0    0    0                                  25    3   .05 20   20   20   0   0    40   50                                 26    3   .05 0    10   0    0   0    50   60                                 __________________________________________________________________________

What is claimed is:
 1. Compounds of pyridine sulfonyl urea derivativeshaving the structure of the following formula(I) ##STR99## wherein, Q isQ-1, Q-2, Q-3 or Q-4 as follows; ##STR100## E is single bond or CH₂ ; R¹is H, C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, halogen, CN, NO₂, C₁ -C₃ alkoxy,C₁ -C₃ haloalkoxy, SO₂ NR^(I) R^(II), C₁ -C₃ alkylthio, C₁ -C₃alkylsulfinyl, C₁ -C₃ alkylsulfonyl, SCH₂ F, NH₂, NHCH₃, N(CH₃)₂, C₁ -C₂alkyl substituted with C₁ -C₂ alkoxy, C₁ -C₂ haloalkoxy, SH, SCH₃, CN orOH or CO₂ R^(III) ; and then R^(I) is H, C₁ -C₄ alkyl, C₂ -C₃cyanoalkyl, methoxy or ethoxy; R^(II) is H, C₁ -C₄ alkyl, C₃ -C₄alkenyl, or when taken together, connecting R^(I) and R^(II), --(CH₂)₃--, --(CH₂)₄ --, --(CH₂)₅ -- or CH₂ CH₂ OCH₂ CH₂ --, may beformed;R^(III) is C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, C₁ -C₄alkyl substituted with 1˜2 halogen or cyano groups, C₅ -C₆, cycloalkyl,C₃ -C₇ cycloalkylalkyl or C₂ -C₄ alkoxyalkyl; R² is C₁ -C₆ alkylsubstituted with 1˜3 halogens; R³ is H or CH₃ ; W is O or S; A is##STR101## wherein, X is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄haloalkoxy, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylthio,halogen, C₂ -C₅ alkoxyalkyl, C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃alkylamino, di(C₁ -C₃ alkyl) amino or C₃ -C₅ cycloalkyl; Y is H, C₁ -C₄alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ haloakylthio, C₁ -C₄alkylthio, C₂ -C₅ alkoxyalkyl, C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃alkylamino, di(C₁ -C₃ alkyl)amino, C₃ -C₄ alkenyloxy, C₂ -C₅alkylthioalkyl, C₁ -C₄ haloalkyl, C₂ -C₄ alkynyl, azido, cyano, C₂ -C₅alkylsulfinylalkyl, C₂ -C₅ alkylsulfonylalkyl, CH₂ OH, C₃ -C₅cycloalkyl, ##STR102## m is 2 or 3, L¹ and L² are independently O or S;R⁴ and R⁵ are independently C₁ -C₂ alkyl; R⁶ is H or CH₃ ; Z is CH; X³is CH₃ or OCH₃ ;or the agriculturally suitable salts thereof.
 2. Acompound as defined in the claim 1, wherein E is single bond, W is O,and R³ is H.
 3. A compound as defined in the claim 1, wherein R¹ isselected from the group consisting of H, halogen, C₁ -C₂ alkyl, C₁ -C₂alkoxy, C₁ -C₂ haloalkyl, C₁ -C₂ alkylthio, haloalkoxy and CH₂ CN; X isselected from the group consisting of C₁ -C₂ alkyl, C₁ -C₂ alkoxy, Cl,F, Br, I, OCHF₂, CH₂ F, CF₃, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃, CH₂ Cl andCH₂ Br; and Y is H, C₁ -C₂ alkyl, C₁ -C₂ alkoxy, CH₂ OCH₃, CH₂ OCH₂ CH₃,NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂OC₂ H₅, OCH₂ CH₂ OCH₃, CH₂ SCH₃, ##STR103## OCHF₂, OCF₂ Br, SCHF₂,cyclopropyl, C.tbd.CH or C.tbd.C--CH₃, and then R⁴ and R⁵ are C₁ -C₂alkyl, R⁶ is H or CH₃, L¹ and L² are O or S and m is 2 or
 3. 4. Acompound as defined in the claim 1, wherein Q is Q-1 or Q-2; Z is CH; Xis CH₃, C₂ H₅, OCH₃, OCH₂ CH₃, Cl or OCHF₂ ; Y is CH₃, OCH₃, OC₂ H₅, C₂H₅, CH₂ OCH₃, NHCH₃, CH(OCH₃)₂ or cyclopropyl.
 5. A compound as definedin the claim 1, wherein R² is CH₂ F, CH₂ CH₂ F, CHF--CH₃, CH₂ Cl, CH₂Br, CHCl₂, CHFCl, CH₂ CH₂ Cl, CHClCH₃, CHF₂, CHCl--CH₂ Cl, CHFCH₂ Cl,CHF--CH₂ F or CH₂ CHF₂.
 6. A compound as defined in claim 1, whereinsaid general formula(I) isN-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(2-fluoro-1-hydroxyethyl)-2-pyridinesulfonamide.7. A compound as defined in claim 1, wherein said general formula(I) is3-(2-fluoro-1-hydroxyethyl)-N-[(4-methoxy-6-methyl-pyrimidin-2-yl)aminocarbonyl]-2-pyridinesulfonamide.8. A compound as defined in claim 1, wherein said general formula(I) isN-[(4-chloro-6-methoxy-pyrimidin-2-yl)aminocarbonyl]-3-(2-fluoro-1-hydroxyethyl)-2-pyridinesulfonamide.9. A compound as defined in claim 1, wherein said general formula(I) isN-[(4,6-dimethyl-pyrimidin-2-yl)aminocarbonyl]-3-(2-fluoro-1-hydroxyethyl)-2-pyridinesulfonamide.10. A compound as defined in claim 1, wherein said general formula(I) isN-[(4-chloro-6-ethoxy-pyrimidin-2-yl)aminocarbonyl]-3-(2-fluoro-1-hydroxyethyl)-2-pyridinesulfonamide.11. A compound as defined in claim 1, wherein said general formula(I) isN-[(4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl]-2-(2-fluoro-1-hydroxyethyl)-3-pyridinesulfonamide.
 12. Acompound as defined in claim 1, wherein said general formula(I) is3-(2-fluoro-1-hydroxypropyl)-N-[(4-methyl-6-methoxy-pyrimidin-2-yl)aminocarbonyl]-2-pyridinesulfonamide.
 13. A compound as defined in claim1, wherein said general formula(I) isN-[(4,6-dimethyl-pyrimidin-2-yl)aminocarbonyl]-3-(2-fluoro-1-hydroxypropyl)-2-pyridinesulfonamide.14. A compound as defined in claim 1, wherein said general formula(I) isN-[(4-chloro-6-methoxy-pyrimidin-2-yl)aminocarbonyl]-3-(-2-fluoro-1-hydroxypropyl)-2-pyridinesulfonamide.
 15. Acompound as defined in claim 1, wherein said general formula(I) isN-[(4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl]-3-(2-chloro-1-hydroxyethyl)-2-pyridinesulfonamide.16. A compound as defined in claim 1, wherein said general formula(I) is3-(2-chloro-1-hydroxyethyl)-N-[(4-methoxy-6-methyl-pyrimidin-2-yl)aminocarbonyl]-2-pyridinesulfonamide.
 17. A compound as defined in claim1, wherein said general formula(I) is3-(2-chloro-1-hydroxyethyl)-N-[(4,6-dimethyl-pyrimidin-2-yl)aminocarbonyl]-2-pyridinesulfonamide.18. A compound as defined in claim 1, wherein said general formula(I) isN-[(4-chloro-6-methoxy-pyrimidin-2-yl)aminocarbonyl]-3-(2-chloro-1-hydroxyethyl)-2-pyridinesulfonamide.19. A compound as defined in claim 1, wherein said general formula(I) is3-(2-fluoro-1-hydroxybutyl)-N-[(4-methoxy-6-methyl-pyrimidin-2-yl)aminocarbonyl]-2-pyridinesulfonamide.
 20. A compound as defined in claim1, wherein said general formula(I) isN-[(4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl]-3-(2-fluoro-1-hydroxybutyl)-2-pyridinesulfonamide.21. A compound as defined in claim 1, wherein said general formula(I) is3-(2-chloro-1-hydroxypropyl)-N-[(4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl]-2-pyridinesulfonamide.
 22. A compound as defined in claim1, wherein said general formula(I) isN-[(4-6-dimethoxy-pyrimidin-2-yl)aminocarbonyl]-3-(2-fluoro-1-hydroxypropyl)-2-pyridinesulfonamide.23. A compound as defined in claim 1, wherein said general formula(I) is3-(2-chloro-1-hydroxyethyl)-N-[(4-chloro-6-ethoxy-pyrimidin-2-yl)aminocarbonyl]-2-pyridinesulfonamide.24. A compound as defined in claim 1, wherein said general formula(I) isN-[(4-chloro-6-ethoxy-pyrimidin-2-yl)aminocarbonyl]-2-(2-fluoro-1-hydroxyethyl)-3-pyridinesulfonamide.25. A compound as defined in claim 1, wherein said general formula(I) is3-(2-chloro-hydroxypropyl)-N-[(4-methoxy-6-methyl-pyrimidin-2-yl)aminocarbonyl]-2-pyridinesulfonamide.26. A compound as defined in claim 1, wherein said general formula(I) isN-[(4-chloro-6-methoxy-pyrimidin-2-yl)aminocarbonyl]-2-(2-fluoro-1-hydroxyethyl)-3-pyridinesulfonamide.27. A compound as defined in claim 1, wherein said general formula(I) isN-[(4,6-dimethoxy-pyrimidin-2-yl)aminocarbonyl]-2-(2-fluoro-1-hydroxypropyl)-3-pyridinesulfonamide.28. Compounds as defined in claim 1, wherein said general formula(I) is2-(2-fluoro-1-hydroxyethyl)-N-[(4-methoxy-6-methyl-pyrimidin-2-yl)aminocarbonyl]-3-pyridinesulfonamide.29. Compounds as defined in claim 1, wherein said general formula(I) isN-[(4,6-dimethyl-pyrimidin-2-yl)aminocarbonyl]-2-(2-fluoro-1-hydroxyethyl)-3-pyridinesulfonamide.30. Compounds as defined in the claim 1, wherein, R¹ is H; R² is CH₂ F,CH₂ Cl, CHF₂, CHFCH₃ or CH₂ CH₂ F; R³ is H; A is A₁ ; and W is O. 31.Intermediate compounds of the formula(I) in the claim 1 having thefollowing formula(II) ##STR104## wherein R¹, R², R³, E, W and A arerespectively as defined in claim 1; Ac is acetyl group or protectedgroup regenerating hydroxy group by separating under the condition ofacid or alkali; ##STR105## with the proviso that R¹ is not a parasubstituent of sulfonyl urea.
 32. A method for controlling weeds bywhich effective amount of one or more of the following formula (I) ofpyridine sulfonyl urea derivatives in weedy area at pre-emergence orpost emergence ##STR106## wherein O, W, R³ and A are respectively asdefined in claim
 1. 33. A herbicidal composition comprising one or morecomponents selected from formula I of claim 1 in combination with aninert carrier.